CN110167919A - The preparation method of 3- aryi-uracile compound - Google Patents
The preparation method of 3- aryi-uracile compound Download PDFInfo
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- CN110167919A CN110167919A CN201880005354.1A CN201880005354A CN110167919A CN 110167919 A CN110167919 A CN 110167919A CN 201880005354 A CN201880005354 A CN 201880005354A CN 110167919 A CN110167919 A CN 110167919A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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Abstract
The present invention relates to the preparation methods of 3- aryi-uracile compound.Preparation method of the invention can prepare reaction time and the solvent usage of 3- aryi-uracile compound by reduction efficiently to prepare 3- aryi-uracile compound.
Description
Technical field
The present invention claims the priority of the South Korea patent application No.10-2017-0002308 submitted on January 6th, 2017
Benefit, all the elements are incorporated herein by quoting.
The present invention relates to the preparation methods of 3- aryi-uracile compound.
Background technique
Food, medicine can produced by organic synthesis by the following formula I V 3- aryi-uracile compound indicated and its salt
It is used as important intermediate in object, agrochemical field:
[formula IV]
(wherein, R1、R2、R4、R5And R7As noted in the discussion).
Made for example, Korean Patent No.1103840 (on January 2nd, 2012) is disclosed using the compound that above-mentioned formula IV indicates
The uracil compounds having following structure are synthesized for intermediate, with activity of weeding.
Therefore, it inventor developed a kind of improved preparation method, is answered for more efficiently synthesizing with various industry
The 3- aryi-uracile compound indicated by formula IV, so as to complete the present invention.
Summary of the invention
Technical problem
The present invention provides a kind of method for efficiently preparing 3- aryi-uracile compound, this method is shortening the reaction time
While reduce the dosage of solvent.
Technical solution
To achieve the goals above, the present invention provides a kind of preparation method of 3- aryi-uracile compound, the sides
Method includes: cyclisation step: in the presence of base, in 80 to 250 DEG C of solvent, passing through the compound of following formula I and Formula Il
The reaction of compound forms the compound of Formula Il I；The change of following formula I V is formed with the alkylation of the compound by above-mentioned formula III
The step of closing object, wherein byproduct of reaction, that is, alcohol (R is continuously being removed from reaction system3OH and R6OH described in being carried out while)
Cyclisation step:
[Formulas I]
[Formula II]
[formula III]
[formula IV]
Wherein in Formulas I into IV, R1It is hydrogen, halogen or alkyl with 1 to 4 carbon atoms,
R2It is alkyl with 1 to 4 carbon atoms, or the halogenated alkyl with 1 to 4 carbon atom,
R3It is alkyl with 1 to 4 carbon atoms,
R4It is halogen or cyano,
R5It is hydrogen or halogen,
R6It is alkyl with 1 to 4 carbon atoms, and
R7It is alkyl with 1 to 4 carbon atoms.
Beneficial effect
Preparation method according to the present invention allows to efficiently prepare 3- aryi-uracile compound, to react shortening
The dosage of solvent is reduced while time.
Specific embodiment
Hereinafter, it will be described in the preparation method of the 3- aryi-uracile compound of embodiment according to the present invention.
Before describing, unless clearly stating in the present specification, otherwise term is only used for referring to particular implementation, and
And it is not intended to be limited to the present invention.
Unless phrase clearly has opposite meaning, otherwise singular used herein includes plural form.
As it is used herein, term " includes " embodies certain features, region, integer, step, operation, element and/or group
Part, and do not preclude the presence or addition of other certain features, region, integer, step, operation, element, component and/or groups.
Meanwhile the result of the lasting research as the present inventor, it was demonstrated that for synthesizing the 3- virtue indicated by formula IV
The cyclisation step of base uracil compound can have in the presence of suitable inorganic or organic base more than or equal to 80 DEG C
High boiling polarity or nonpolar solvent in carry out, at this point, when continuously removing the i.e. alcohol of byproduct of reaction from reaction system,
3- aryi-uracile compound can be efficiently prepared, to reduce the dosage of solvent while shortening the reaction time.
According to embodiment of the present invention, the present invention provides a kind of preparation sides of 3- aryi-uracile compound
Method, which comprises cyclisation step: in the presence of base, in 80 to 250 DEG C of solvent, by the compound of following formula I with
The reaction of the compound of Formula Il forms the compound of Formula Il I；Alkylation with the compound by formula III above forms following formula
The step of compound of IV, wherein byproduct of reaction, that is, alcohol (R is continuously being removed from reaction system3OH and R6OH while) into
The row cyclisation step:
[Formulas I]
[Formula II]
[formula III]
[formula IV]
Wherein in Formulas I into IV, R1 is hydrogen, halogen or alkyl with 1 to 4 carbon atoms, and preferably can be hydrogen；
R2Alkyl with 1 to 4 carbon atoms, or the halogenated alkyl with 1 to 4 carbon atom, and preferably can be with 1 to
The halogenated alkyl of 4 carbon atoms: R3、R6And R7Individually alkyl with 1 to 4 carbon atoms: R4It is halogen or cyano, and
It is preferred that can be halogen；And R5It is hydrogen or halogen, and preferably can be halogen.
The 3- aryi-uracile compound and its salt that above-mentioned formula IV indicates can produce food, medicine by organic synthesis
It is used as important intermediate in object, agrochemical field.
In particular, the compound of formula IV has activity of weeding, and the active matter cut weeds with composition can be suitable as
Matter or in which mesosome.
According to embodiment of the present invention, the compound of formula IV can be prepared by the following: (i) passes through Formulas I
Compound and Formula II compound cyclization formed formula III compound；The alkane that (ii) passes through the compound of formula III
Baseization formed correspond to above-mentioned formula IV N- substituted compound (wherein alkyl is introduced in the unsubstituted nitrogen-atoms of uridine diphosphate
On compound).In addition, in the cyclization of Formulas I and II compound, alcohol (R3OH and R6OH it) is generated as byproduct of reaction.
In particular, according to embodiment of the present invention, cyclisation step carries out in the presence of (a) suitable alkali, (b) exist
With being carried out in 80 DEG C or more high boiling polarity or nonpolar solvent, (c) continuously remove from reaction system simultaneously and react by-product
Object, i.e. alcohol (R3OH and R6OH).As a result, in cyclisation step, since the dosage of solvent can be reduced to less than half, and it is anti-
Significantly shorten between seasonable, therefore the efficient of the 3- aryi-uracile compound of formula IV is prepared into possibility.
Specifically, according to embodiment of the present invention, it in cyclisation step, when meeting condition (b) and (c), removes
Common potassium carbonate (K2CO3) other than, even if using such as sodium carbonate (Na2CO3), cesium carbonate (Cs2CO3), saleratus
(KHCO3) or sodium bicarbonate (NaHCO3) etc. inorganic bases also can be realized excellent reaction efficiency as alkali.
In addition, organic base such as 1,8- diazabicyclo [5.4.0] ten can be used when meeting above-mentioned condition (b) and (c)
One carbon -7- alkene is as the alkali in cyclisation step.
That is, according to embodiment of the present invention, the alkali in cyclization step can be selected from by following
At least one of the group of compound composition compound: potassium carbonate (K2CO3), sodium carbonate (Na2CO3), cesium carbonate (Cs2CO3), carbon
Potassium hydrogen phthalate (KHCO3), sodium bicarbonate (NaHCO3) and 11 carbon -7- alkene of 1,8- diazabicyclo [5.4.0].
In addition, according to embodiment of the present invention, when meeting condition (a) and (c), the solvent in cyclisation step can
To be polar solvent, such as n,N-Dimethylformamide (boiling point is 152 to 154 DEG C), n-methyl-2-pyrrolidone (boiling point 202
To 204 DEG C) and dimethyl sulfoxide (boiling point is 189 DEG C)；Or nonpolar solvent, such as methyl butyl diethylene glycol (DEG) (boiling point is 211.4 DEG C)
With o-dichlorohenzene (boiling point is 180.5 DEG C).
By the solvent that selects in application examples detailed above, cyclisation step can 80 DEG C or more, 80 to 250 DEG C, 100 to
It is carried out at a high temperature of 230 DEG C, 120 to 220 DEG C or 130 to 210 DEG C, but not limited to this.
In particular, if being directed to cyclisation step application nonpolar solvent, such as methyl butyl diethylene glycol (DEG) and o-dichlorohenzene, then
When carrying out cyclisation step, generation is separated with the layer of polar layer (such as water layer), thus can easily recycling design, and lead to
Crossing recycling recovered solvent can be improved production efficiency.
In addition, according to embodiment of the present invention, the additional amount of the solvent in cyclisation step can be the chemical combination of Formulas I
0.5 to 15 times of object weight, 1 to 10 times or 1 to 6.1 times, but not limited to this.
In particular, when meeting above-mentioned condition (a) and (b), if continuously removing byproduct of reaction i.e. from reaction system
Alcohol (R3OH and R6OH it is cyclized while), then the dosage of solvent can be reduced to less than half, and the simultaneous reactions time significantly subtracts
It is few, therefore can more efficiently obtain 3- aryi-uracile compound.
For example, while the cyclization of the compound of the compound and Formula II by Formulas I forms the compound of formula III
Cyclisation step is carried out, its byproduct of reaction, i.e. alcohol (R are continuously removed from reaction system by distillation at the same time3OH and
R6OH)。
Distillating method progress can be used in the cyclisation step.
Preferably, cyclisation step can be with the N for the weight addition for being 3.5 times relative to the compound of Formulas I, N- diformazan
In inorganic base potassium carbonate (K in the solvent of base formamide2CO3) in the presence of carry out, while from reaction system continuously removal reaction
By-product alcohol.
Moreover it is preferred that cyclisation step can with relative to the compound of Formulas I be 1.5 times weight be added N,
In inorganic base potassium carbonate (K in the solvent of dinethylformamide2CO3) in the presence of carry out, while continuously being gone from reaction system
Except byproduct of reaction alcohol.
Moreover it is preferred that cyclisation step can with relative to the compound of Formulas I be 1.5 times weight be added N,
In inorganic bases sodium carbonate (Na in the solvent of dinethylformamide2CO3) in the presence of carry out, while from reaction system continuously
Remove byproduct of reaction alcohol.
Moreover it is preferred that cyclisation step can with relative to the compound of Formulas I be 1.5 times weight be added N,
In inorganic base cesium carbonate (Cs in the solvent of dinethylformamide2CO3) in the presence of carry out, while from reaction system continuously
Remove byproduct of reaction alcohol.
Moreover it is preferred that cyclisation step can with relative to the compound of Formulas I be 1.5 times weight be added N,
In inorganic base saleratus (KHCO in the solvent of dinethylformamide3) in the presence of carry out, while it is continuous from reaction system
Ground removes byproduct of reaction alcohol.
Moreover it is preferred that cyclisation step can with relative to the compound of Formulas I be 1.5 times weight be added N,
In inorganic base sodium bicarbonate (NaHCO in the solvent of dinethylformamide3) in the presence of carry out, while it is continuous from reaction system
Ground removes byproduct of reaction alcohol.
Moreover it is preferred that cyclisation step can with relative to the compound of Formulas I be 1.5 times weight be added N,
It is carried out in the presence of organic base 1,11 carbon -7- alkene of 8- diazabicyclo [5.4.0] in the solvent of dinethylformamide, simultaneously
Byproduct of reaction alcohol is continuously removed from reaction system.
Moreover it is preferred that cyclisation step can be with the N- for the weight addition for being 1.5 times relative to the compound of Formulas I
In inorganic base potassium carbonate (K in the solvent of N-methyl-2-2-pyrrolidone N2CO3) in the presence of carry out, while from reaction system continuously
Remove byproduct of reaction alcohol.
Moreover it is preferred that cyclisation step can be with the two of the weight addition for being 1.5 times relative to the compound of Formulas I
In inorganic base potassium carbonate (K in the solvent of first sulfoxide2CO3) in the presence of carry out, while continuously removal reaction is secondary from reaction system
Product alcohol.
Moreover it is preferred that cyclisation step can be with the first for the weight addition for being 6.1 times relative to the compound of Formulas I
In inorganic base potassium carbonate (K in the solvent of base butyldiglycol2CO3) in the presence of carry out, while continuously being removed from reaction system
Byproduct of reaction alcohol.
Moreover it is preferred that cyclisation step can be with the neighbour for the weight addition for being 1.5 times relative to the compound of Formulas I
In inorganic base potassium carbonate (K in the solvent of dichloro-benzenes2CO3) in the presence of carry out, while continuously removal reaction is secondary from reaction system
Product alcohol.
Meanwhile after completing cyclisation, product can have the shape of metal salt corresponding with above-mentioned formula III or organic salt
Formula.
The compound of formula III is converted to the compound of the N- substitution corresponding to formula IV by alkylation.Art used herein
Language " alkylation " refers to alkyl with 1 to 4 carbon atoms (R7) it is introduced into not taking for uridine diphosphate in the compound of formula III
On the nitrogen-atoms in generation.
According to embodiment of the present invention, in alkylating agent such as dialkyl sulfate or with 1 to 4 carbon atom
In the presence of alkyl halide, abovementioned alkyl step can be carried out continuously in the case where not changing solvent, or molten being added
It is carried out continuously while agent such as methylene chloride, 1,2- dichloroethanes and toluene.
The 3- aryi-uracile compound of formula IV can be prepared by a series of cyclisation as described above and alkylation step.
Conventional steps, for example, reactant purifying and product separation can cyclisation step and alkylation step etc. it
Before/be additionally carried out later.
Hereinafter, preferred embodiment is listed in order to understand the present invention.However, following embodiment is intended to illustrate hair
Bright, but the invention is not restricted to this.
Embodiment 1
Potassium carbonate (227.9g, 1.649mol), following formula I ' compound (3- amino -4,4,4- trifluoroacetic ethyl crotonate,
114.4g, 0.625mol) and Formula Il ' compound (N- (the chloro- 2- fluorophenyl of 4-) urethanes, 149.5g,
It 0.687mol) is added in n,N-Dimethylformamide (400.3g), then the temperature range by mixture at 130 to 135 DEG C
Heating stirring 4 hours.Associated temperature is kept by distilling, continuously removes the by-product (EtOH) formed in whipping process.
After being analyzed to identify the formation for completing the compound of Formula Il I' by HPLC, alkyl is just carried out without purification process
Change reaction.After the temperature of reactant is cooled to 0 to 5 DEG C, in 1 hour be added dropwise dimethyl suflfate (173.3g,
1.374mol).Reaction mixture is 1 hour stirred below at 30 DEG C.Water is added into reaction mixture, is precipitated as product solid
Body.Solid is washed and is dried with hexane, obtain formula IV ' compound, be pale solid (172.3g, 85.5%).
1H NMR(400MHz,CDCl3) δ 7.19~7.32 (m, 3H), 6.39 (s, 1H), 3.58 (s, 3H).
[Formulas I ']
[Formula II ']
[formula III ']
[formula IV ']
Embodiment 2
Formula III ' compound obtain according to the same manner as in Example 1, the difference is that in cyclisation, as anti-
Answer the N,N-dimethylformamide of solvent relative to Formulas I ' compound be 1.5 times weight be added.
It is cyclized and completes after 3 hours, it is about 1 hour shorter than embodiment 1.
Then, pass through the formula III of mode same as Example 1 ' compound alkylation obtain formula IV ' compound
(85.6%).
Embodiment 3
Formula III ' compound obtain according to the same manner as in Example 1, the difference is that in cyclisation, sodium carbonate
(Na2CO3) replace potassium carbonate (K2CO3) as alkali be added, and as the n,N-Dimethylformamide of reaction dissolvent with relative to
Formulas I ' compound be 1.5 times weight be added.
It is cyclized and completes after about 4 hours.
Then, pass through the formula III of mode same as Example 1 ' compound alkylation obtain formula IV ' compound
(90.6%).
Embodiment 4
Formula III ' compound obtain according to the same manner as in Example 1, the difference is that in cyclisation, sodium carbonate
(Na2CO3) replace potassium carbonate (K2CO3) as alkali be added, and as the n,N-Dimethylformamide of reaction dissolvent with relative to
Formulas I ' compound be 1.5 times weight be added.
It is cyclized and completes after about 6.5 hours.
Then, pass through the formula III of mode same as Example 1 ' compound alkylation obtain formula IV ' compound
(75.2%).
Embodiment 5
Formula III ' compound obtain according to the same manner as in Example 1, the difference is that in cyclisation, bicarbonate
Potassium (KHCO3) replace potassium carbonate (K2CO3) be added as alkali, and the n,N-Dimethylformamide as reaction dissolvent is with opposite
In Formulas I ' compound be 1.5 times weight be added.
It is cyclized and completes after about 4 hours.
Then, pass through the formula III of mode same as Example 1 ' compound alkylation obtain formula IV ' compound
(82.1%).
Embodiment 6
Formula III ' compound obtain according to the same manner as in Example 1, the difference is that in cyclisation, cesium carbonate
(Cs2CO3) replace potassium carbonate (K2CO3) as alkali be added, and as the n,N-Dimethylformamide of reaction dissolvent with relative to
Formulas I ' compound be 1.5 times weight be added.
It is cyclized and completes after about 3.5 hours.
Then, pass through the formula III of mode same as Example 1 ' compound alkylation obtain formula IV ' compound
(81.8%).
Embodiment 7
Formula III ' compound obtain according to the same manner as in Example 1, the difference is that in cyclisation, 1,8- bis-
11 carbon -7- alkene of azabicyclo [5.4.0] replaces potassium carbonate (K2CO3) be added as alkali, and the N as reaction dissolvent, N- bis-
Methylformamide is relative to Formulas I ' compound be 1.5 times weight be added.
It is cyclized and completes after about 3.5 hours.
Then, pass through the formula III of mode same as Example 1 ' compound alkylation obtain formula IV ' compound
(85.8%).
Embodiment 8
Formula III ' compound obtain according to the same manner as in Example 1, the difference is that in cyclisation, methyl fourth
Base diethylene glycol (DEG) (MBDG) replace N,N-dimethylformamide as reaction dissolvent relative to Formulas I ' compound be 6.1 times of weight
Amount be added, and be cyclized 210 DEG C at a temperature of carry out.
It is cyclized and completes after about 4 hours.
Then, carry out formula III ' compound alkylated reaction after by washing and concentration, according to 1 phase of embodiment
Same mode recycling design.Concentration reaction product wash and is dried with hexane, and formula IV is obtained ' compound, for pale solid
(78.6%).
Embodiment 9
Formula III ' compound obtain according to the same manner as in Example 1, the difference is that in cyclisation, adjacent dichloro
Benzene (ODCB) substitutes N,N-dimethylformamide as reaction dissolvent relative to Formulas I ' compound add for 1.5 times of weight
Enter, and be cyclized 170 to 180 DEG C at a temperature of carry out.
It is cyclized and completes after about 4 hours.
Then, carry out formula III ' compound alkylated reaction after by washing and concentration, according to 1 phase of embodiment
Same mode recycling design.Concentration reaction product is washed and is dried with hexane, obtain formula IV ' compound formula IV ' compound
(84.7%).
Embodiment 10
Formula III ' compound obtain according to the same manner as in Example 1, the difference is that in cyclisation, N- first
Base -2-Pyrrolidone (NMP) substitute N,N-dimethylformamide as reaction dissolvent relative to Formulas I ' compound be 1.5 times
Weight be added.
It is cyclized and completes after about 2.5 hours.
Then, pass through the formula III of mode same as Example 1 ' compound alkylation obtain formula IV ' compound
(70.0%).
Embodiment 11
Formula III ' compound obtain according to the same manner as in Example 1, the difference is that in cyclisation, diformazan is sub-
Sulfone (DMSO) substitutes N,N-dimethylformamide as reaction dissolvent relative to Formulas I ' compound add for 1.5 times of weight
Enter.
It is cyclized and completes after about 2.5 hours.
Then, pass through the formula III of mode same as Example 1 ' compound alkylation obtain formula IV ' compound
(85.3%).
Comparative example 1
Formula III ' compound obtain according to the same manner as in Example 1, the difference is that in cyclisation not into
The distillation of row removal byproduct of reaction (ethyl alcohol).
Cyclisation is completed after 8 hours, postpones about 4 hours compared with Example 1.
Then, pass through the formula III of mode same as Example 1 ' compound alkylation obtain formula IV ' compound
(85.0%).
Comparative example 2
Formula III ' compound obtain according to the same manner as in Example 1, the difference is that in cyclisation, as anti-
Answer the n,N-Dimethylformamide of solvent relative to Formulas I ' compound be 1.5 times weight be added, and do not gone
Except the distillation of byproduct of reaction (ethyl alcohol).
Cyclisation is completed after 22 hours, postpones about 18 hours compared with Example 1.
Then, pass through the formula III of mode same as Example 1 ' compound alkylation obtain formula IV ' compound
(84.4%).
Claims (5)
1. a kind of preparation method of 3- aryi-uracile compound, which comprises
Cyclisation step: in the presence of base, in 80 to 250 DEG C of solvent, pass through the compound of following formula I and the chemical combination of Formula Il
The reaction of object forms the compound of Formula Il I, and
The step of forming the compound of following formula I V by the alkylation of the compound of formula III；Wherein, continuous from reaction system
Remove byproduct of reaction, that is, alcohol (R3OH and R6OH the cyclisation step is carried out while):
[Formulas I]
[Formula II]
[formula III]
[formula IV]
Wherein in Formulas I into IV, R1It is hydrogen, halogen or alkyl with 1 to 4 carbon atoms,
R2It is alkyl with 1 to 4 carbon atoms or the halogenated alkyl with 1 to 4 carbon atom,
R3It is alkyl with 1 to 4 carbon atoms,
R4It is halogen or cyano,
R5It is hydrogen or halogen,
R6It is alkyl with 1 to 4 carbon atoms, and
R7It is alkyl with 1 to 4 carbon atoms.
2. the alkali is selected from by following compound group the method for claim 1, wherein in the cyclisation step
At at least one of group compound: potassium carbonate (K2CO3), sodium carbonate (Na2CO3), cesium carbonate (Cs2CO3), saleratus
(KHCO3), sodium bicarbonate (NaHCO3) and 11 carbon -7- alkene of 1,8- diazabicyclo [5.4.0].
3. the method for claim 1, wherein the cyclisation step carries out in polar solvent, the polar solvent is
N,N-dimethylformamide, n-methyl-2-pyrrolidone or dimethyl sulfoxide.
4. the method for claim 1, wherein the cyclisation step carries out in nonpolar solvent, the nonpolarity is molten
Agent is methyl butyl diethylene glycol (DEG) or o-dichlorohenzene.
5. the method for claim 1, wherein in the cyclisation step, the compound relative to Formulas I be added 0.5 to
The solvent of 15 times of weight.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020170002308A KR20180081275A (en) | 2017-01-06 | 2017-01-06 | Method for producing 3-aryluracils compound |
| KR10-2017-0002308 | 2017-01-06 | ||
| PCT/KR2018/000122 WO2018128387A1 (en) | 2017-01-06 | 2018-01-03 | Method for producing 3-aryl uracil compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110167919A true CN110167919A (en) | 2019-08-23 |
Family
ID=62789368
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201880005354.1A Withdrawn CN110167919A (en) | 2017-01-06 | 2018-01-03 | The preparation method of 3- aryi-uracile compound |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR20180081275A (en) |
| CN (1) | CN110167919A (en) |
| WO (1) | WO2018128387A1 (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4859229A (en) * | 1986-07-31 | 1989-08-22 | Hoffmann-La Roche Inc. | 3-Aryluracils having an ether (thio) carbomyloxy or sulphomyloxy substituent on the aromatic moiety |
| EP0831091A2 (en) * | 1996-09-23 | 1998-03-25 | Novartis AG | Process for the production of 3-aryl-uracils |
| US20020010334A1 (en) * | 2000-06-30 | 2002-01-24 | Xun Li | Processes to prepare pyrimidinediones |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3089621B2 (en) * | 1990-12-17 | 2000-09-18 | 日産化学工業株式会社 | Uracil derivatives |
| DE19644534C2 (en) * | 1996-10-26 | 2001-03-22 | Vaupel Textilmaschinen Gmbh & | Device for longitudinally cutting a meltable broad web into at least two tapes, in particular into patterned label tapes |
| WO2005054208A1 (en) * | 2003-12-03 | 2005-06-16 | Basf Aktiengesellschaft | Method for producing 3-phenyl(thio)uracils and 3-phenyldithiouracils |
-
2017
- 2017-01-06 KR KR1020170002308A patent/KR20180081275A/en active Search and Examination
-
2018
- 2018-01-03 WO PCT/KR2018/000122 patent/WO2018128387A1/en active Application Filing
- 2018-01-03 CN CN201880005354.1A patent/CN110167919A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4859229A (en) * | 1986-07-31 | 1989-08-22 | Hoffmann-La Roche Inc. | 3-Aryluracils having an ether (thio) carbomyloxy or sulphomyloxy substituent on the aromatic moiety |
| EP0831091A2 (en) * | 1996-09-23 | 1998-03-25 | Novartis AG | Process for the production of 3-aryl-uracils |
| US20020010334A1 (en) * | 2000-06-30 | 2002-01-24 | Xun Li | Processes to prepare pyrimidinediones |
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| WO2018128387A1 (en) | 2018-07-12 |
| KR20180081275A (en) | 2018-07-16 |
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