JPS626707B2 - - Google Patents
Info
- Publication number
- JPS626707B2 JPS626707B2 JP1550482A JP1550482A JPS626707B2 JP S626707 B2 JPS626707 B2 JP S626707B2 JP 1550482 A JP1550482 A JP 1550482A JP 1550482 A JP1550482 A JP 1550482A JP S626707 B2 JPS626707 B2 JP S626707B2
- Authority
- JP
- Japan
- Prior art keywords
- amino
- alkyl
- formylpyrimidine
- methyl
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002253 acid Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- DPOYRRAYGKTRAU-UHFFFAOYSA-N 2-aminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C=N1 DPOYRRAYGKTRAU-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- NOHYIPRJOCCNMG-UHFFFAOYSA-N 4-amino-2-methylpyrimidine-5-carbaldehyde Chemical compound CC1=NC=C(C=O)C(N)=N1 NOHYIPRJOCCNMG-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- WPNRPBRVBAICQQ-UHFFFAOYSA-N 5-(dimethoxymethyl)-2-methylpyrimidin-4-amine Chemical compound COC(OC)C1=CN=C(C)N=C1N WPNRPBRVBAICQQ-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- -1 2-methyl-4-amino-5-dimethoxymethylpyrimidine Pyrimidine Chemical compound 0.000 description 1
- VTHFPIHRGHVRGB-UHFFFAOYSA-N 4-amino-2-ethylpyrimidine-5-carbaldehyde Chemical compound CCC1=NC=C(C=O)C(N)=N1 VTHFPIHRGHVRGB-UHFFFAOYSA-N 0.000 description 1
- HEPMEJCHTBWKIB-UHFFFAOYSA-N 5-(dibutoxymethyl)-2-methylpyrimidin-4-amine Chemical compound CCCCOC(OCCCC)C1=CN=C(C)N=C1N HEPMEJCHTBWKIB-UHFFFAOYSA-N 0.000 description 1
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RXKUYBRRTKRGME-UHFFFAOYSA-N butanimidamide Chemical compound CCCC(N)=N RXKUYBRRTKRGME-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- GNFWGDKKNWGGJY-UHFFFAOYSA-N propanimidamide Chemical compound CCC(N)=N GNFWGDKKNWGGJY-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000011691 vitamin B1 Substances 0.000 description 1
Description
【発明の詳細な説明】
本発明は、２―アルキル―４―アミノ―５―ホ
ルミルピリミジンの新規製法に関するものであ
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a new method for producing 2-alkyl-4-amino-5-formylpyrimidine.
２―アルキル―４―アミノ―５―ホルミルピリ
ミジンは、例えば還元アミノ化することによつ
て、ビタミンB1の合成中間体として重要な化合
物である、２―アルキル―４―アミノ―５―アミ
ノメチルピリミジンに変換することができる。 2-Alkyl-4-amino-5-formylpyrimidine can be converted into 2-alkyl-4-amino-5-aminomethyl, which is an important compound as a synthetic intermediate for vitamin B1 , by reductive amination, for example. Can be converted to pyrimidine.
従来、２―アルキル―４―アミノ―５―ホルミ
ルピリミジンの製法としてChem.Ber.1063743
（1973）に、次の方法が開示されている。 Conventionally, Chem.Ber. 106 3743 was used as a method for producing 2-alkyl-4-amino-5-formylpyrimidine.
(1973) discloses the following method.
まず２―アルキル―４，６―ジクロロ―５―ホ
ルミルピリミジンをアンモニアと反応させ、得ら
れる２―アルキル―４―アミノ―５―ホルミル―
６―クロロピリミジンを水素と反応させ、目的物
の２―アルキル―４―アミノ―５―ホルミルピリ
ミジンを得る。この方法では、反応工程が長く複
雑であり、出発原料の２―アルキル―４，６―ジ
クロロ―５―ホルミルピリミジンの合成が容易で
ない、などの欠点を有している。 First, 2-alkyl-4,6-dichloro-5-formylpyrimidine is reacted with ammonia to obtain 2-alkyl-4-amino-5-formyl-
6-chloropyrimidine is reacted with hydrogen to obtain the target product, 2-alkyl-4-amino-5-formylpyrimidine. This method has drawbacks such as the reaction steps are long and complicated, and the synthesis of the starting material 2-alkyl-4,6-dichloro-5-formylpyrimidine is not easy.
また別法として、C.A.50 7809（1956）に、
２―アルキル―４―アミノ―５―シアノピリミジ
ンを原料とし、希塩酸水溶液中でパラジウム触媒
の存在下に、水素と反応させ、２―アルキル―４
―アミノ―５―ホルミルピリミジンを製造する方
法が提案されている。この方法では、目的物の収
率が極めて低く、しかも目的物の精製のために一
旦ニツケルとの錯体を形成させた後、塩分解を行
なうなど後処理が煩雑である、など工業的に問題
点を有している。 Alternatively, CA 50 7809 (1956)
Using 2-alkyl-4-amino-5-cyanopyrimidine as a raw material, it is reacted with hydrogen in a dilute aqueous hydrochloric acid solution in the presence of a palladium catalyst to produce 2-alkyl-4
A method for producing -amino-5-formylpyrimidine has been proposed. This method has industrial problems such as extremely low yield of the target product and complicated post-treatments such as salt decomposition after once forming a complex with nickel to purify the target product. have.
本発明者らは、これらの実情に鑑み、２―アル
キル―４―アミノ―５―ホルミルピリミジンの工
業的有利な製法を確立することを目的として鋭意
研究を行なつた。 In view of these circumstances, the present inventors conducted extensive research with the aim of establishing an industrially advantageous method for producing 2-alkyl-4-amino-5-formylpyrimidine.
その結果、一般式（）
〔ただし、（）式におけるR1，R2およびR3
は、同一または相異なる低級アルキル基を示
す。〕で表わされる２―アルキル―４―アミノ―
５―ジアルコキシメチルピリミジンを、酸の存在
下に加水分解すれば、極めて工業的有利に、一般
式（）
〔ただし、（）式におけるR1は、低級アルキ
ル基を示す。〕で表わされる、２―アルキル―４
―アミノ―５―ホルミルピリミジンを製造するこ
とができることを知見し、本発明を完成するに到
つた。 As a result, the general formula () [However, R 1 , R 2 and R 3 in formula ()
represent the same or different lower alkyl groups. ] 2-alkyl-4-amino-
If 5-dialkoxymethylpyrimidine is hydrolyzed in the presence of an acid, the general formula () can be obtained with great industrial advantage. [However, R 1 in formula () represents a lower alkyl group. ], 2-alkyl-4
It was discovered that -amino-5-formylpyrimidine can be produced, and the present invention was completed.
本発明の原料である。前記一般式（）で表わ
される２―アルキル―４―アミノ―５―ジアルコ
キシメチルピリミジンにおける、R1，R2および
R3はメチル、エチル、プロピルおよびブチルな
どの低級アルキル基を挙げることができる。これ
らR1，R2およびR3は、全て同一の基であつても
よく、一部同一の基であつてもよく、さらには全
て別々の基であることもできる。これら本発明に
おける原料は、例えば２―ジアルコキシメチル―
３，３―ジアルコキシプロパンニトリルあるいは
２―アルコキシメチレン―３，３―ジアルコキシ
プロパンニトリルと、アセトアミジン、プロピオ
アミジンあるいはブタノアミジンなどのアミジン
類と反応させることにより、容易に合成すること
ができる。 It is the raw material of the present invention. R 1 , R 2 and in 2-alkyl-4-amino-5-dialkoxymethylpyrimidine represented by the general formula ()
R 3 can include lower alkyl groups such as methyl, ethyl, propyl and butyl. These R 1 , R 2 and R 3 may all be the same group, may be partially the same group, or may be all different groups. These raw materials in the present invention are, for example, 2-dialkoxymethyl-
It can be easily synthesized by reacting 3,3-dialkoxypropanenitrile or 2-alkoxymethylene-3,3-dialkoxypropanenitrile with amidines such as acetamidine, propioamidine, or butanoamidine.
本発明において使用に供される酸としては、例
えば塩酸、硫酸、硝酸、リン酸などの鉱酸やＰ―
トルエンスルホン酸、陽イオン交換樹脂などを挙
げることができる。これらの酸は、２―アルキル
―４―アミノ―５―ジアルコキシメチルピリミジ
ンに対して、0.5〜20当量、好ましくは１〜10当
量になるように用いられる。また加水分解に使用
される水の量は、特別制限はないが、通常２―ア
ルキル―４―アミノ―５―ジアルコキシメチルピ
リミジン１重量部に対し１〜200重量部、好まし
くは５〜100重量部用いられる。 Examples of acids that can be used in the present invention include mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid;
Examples include toluenesulfonic acid and cation exchange resins. These acids are used in an amount of 0.5 to 20 equivalents, preferably 1 to 10 equivalents, relative to 2-alkyl-4-amino-5-dialkoxymethylpyrimidine. The amount of water used for hydrolysis is not particularly limited, but is usually 1 to 200 parts by weight, preferably 5 to 100 parts by weight, per 1 part by weight of 2-alkyl-4-amino-5-dialkoxymethylpyrimidine. part is used.
加水分解の条件は、原料の濃度、酸量などに応
じて適宜選択されるが、通常、室温〜100℃の温
度で0.1〜24時間行なうことにより、前記一般式
（）で表わされる２―アルキル―４―アミノ―
５―ホルミルピリミジンを、ほぼ定量的に得るこ
とができる。 The conditions for hydrolysis are appropriately selected depending on the concentration of the raw materials, the amount of acid, etc., but usually the 2-alkyl represented by the general formula () is -4-Amino-
5-formylpyrimidine can be obtained almost quantitatively.
反応終了後、目的物の２―アルキル―４―アミ
ノ―５―ホルミルピリミジンは、例えば過、濃
縮、抽出、再結晶などの操作を適宜採用すること
により、容易に単離、精製することができる。 After completion of the reaction, the target 2-alkyl-4-amino-5-formylpyrimidine can be easily isolated and purified by appropriate operations such as filtration, concentration, extraction, and recrystallization. .
次に、本発明の実施例を挙げる。 Next, examples of the present invention will be given.
実施例 １
２―メチル―４―アミノ―５―ジメトキシメチ
ルピリミジン4.60ｇ（25.1ミリモル）を、1N―
HCl30mlに溶かし、液温を約45〜50℃に保持し約
90分間撹拌した後、室温まで冷却した。次いで、
1N―NaOH約30mlを少しずつ加え中和した後、析
出した結晶を取し、水洗後約50℃で真空乾燥
し、白色結晶の２―メチル―４―アミノ―５―ホ
ルミルピリミジン3.15ｇを得た。さらに液を濃
縮し、析出してきた結晶を熱湯から再結晶した
後、約50℃で真空乾燥し、白色結晶の２―メチル
―４―アミノ―５―ホルミルピリミジン0.15ｇを
得た。Example 1 4.60 g (25.1 mmol) of 2-methyl-4-amino-5-dimethoxymethylpyrimidine was added to 1N-
Dissolve in 30ml of HCl, maintain the liquid temperature at about 45-50℃, and
After stirring for 90 minutes, it was cooled to room temperature. Then,
After neutralizing by adding approximately 30 ml of 1N-NaOH little by little, the precipitated crystals were collected, washed with water, and vacuum dried at approximately 50°C to obtain 3.15 g of 2-methyl-4-amino-5-formylpyrimidine as white crystals. Ta. The liquid was further concentrated, and the precipitated crystals were recrystallized from hot water and then vacuum dried at about 50°C to obtain 0.15 g of 2-methyl-4-amino-5-formylpyrimidine as white crystals.
２―メチル―４―アミノ―５―ホルミルピリミ
ジンの収率：96％
実施例 ２
２―メチル―４―アミノ―５―ジメトキシメチ
ルピリミジンの代りに、２―エチル―４―アミノ
―５―ジメトキシメチルピリミジン4.93ｇ（25.0
ミリモル）を用いた他は、実施例１と同様の操作
で実験を行なつた。その結果、２―エチル―４―
アミノ―５―ホルミルピリミジン3.66ｇ（収率97
％）が得られた。 Yield of 2-methyl-4-amino-5-formylpyrimidine: 96% Example 2 2-ethyl-4-amino-5-dimethoxymethyl instead of 2-methyl-4-amino-5-dimethoxymethylpyrimidine Pyrimidine 4.93g (25.0
The experiment was conducted in the same manner as in Example 1, except that 1 mmol) was used. As a result, 2-ethyl-4-
Amino-5-formylpyrimidine 3.66g (yield 97
%)was gotten.
実施例 ３
２―メチル―４―アミノ―５―ジメトキシメチ
ルピリミジン4.60ｇ（25.1ミリモル）を、1N―
H2SO430mlに溶かし、撹拌下、液温を室温に６時
間保つた。反応液を内部標準法により、液体クロ
マトグラフイーで定量分析した結果、２―メチル
―４―アミノ―５―ホルミルピリミジンが3.42ｇ
（収率：99.5ｇ）生成していることが確認され
た。Example 3 4.60 g (25.1 mmol) of 2-methyl-4-amino-5-dimethoxymethylpyrimidine was added to 1N-
The mixture was dissolved in 30 ml of H 2 SO 4 and the temperature of the solution was kept at room temperature for 6 hours while stirring. As a result of quantitative analysis of the reaction solution by liquid chromatography using the internal standard method, 3.42 g of 2-methyl-4-amino-5-formylpyrimidine was found.
(Yield: 99.5g) It was confirmed that it was produced.
実施例 ４
２―メチル―４―アミノ―５―ジメトキシメチ
ルピリミジンに代えて、２―メチル―４―アミノ
―５―ジエトキシメチルピリミジン5.28ｇ（25.0
ミリモル）を用いた他は、実施例３と同様の操作
で実験を行なつた。その結果、２―メチル―４―
アミノ―５―ホルミルピリミジン3.40ｇ（収率：
99.2％）が得られた。Example 4 In place of 2-methyl-4-amino-5-dimethoxymethylpyrimidine, 5.28 g (25.0
The experiment was conducted in the same manner as in Example 3, except that 1 mmol) was used. As a result, 2-methyl-4-
Amino-5-formylpyrimidine 3.40g (yield:
99.2%) was obtained.
実施例 ５
２―メチル―４―アミノ―５―ジ―ｎ―ブトキ
シメチルピリミジン6.68ｇ（25.0ミリモル）を1N
―HCl30mlに溶かし、液温を約50〜55℃に保持し
約１時間撹拌した。反応液を実施例２と同様にし
て定量した結果、２―メチル―４―アミノ―５―
ホルミルピリミジン3.39ｇ（収率：99.0％）の生
成が確認された。Example 5 6.68 g (25.0 mmol) of 2-methyl-4-amino-5-di-n-butoxymethylpyrimidine was added to 1N
-Dissolved in 30ml of HCl and stirred for about 1 hour while maintaining the liquid temperature at about 50-55℃. As a result of quantifying the reaction solution in the same manner as in Example 2, 2-methyl-4-amino-5-
Production of 3.39 g (yield: 99.0%) of formylpyrimidine was confirmed.
Claims (1)
は、同一または相異なる低級アルキル基を示
す。〕で表わされる２―アルキル―４―アミノ―
５―ジアルコキシメチルピリミジンを、酸の存在
下に加水分解することを特徴とする、一般式
（） 〔ただし、（）式におけるR1は、低級アルキ
ル基を示す。〕で表わされる、２―アルキル―４
―アミノ―５―ホルミルピリミジンの製法。[Claims] 1 General formula () [However, R 1 , R 2 and R 3 in formula ()
represent the same or different lower alkyl groups. ] 2-alkyl-4-amino-
General formula () characterized by hydrolyzing 5-dialkoxymethylpyrimidine in the presence of an acid [However, R 1 in formula () represents a lower alkyl group. ], 2-alkyl-4
-Production method of amino-5-formylpyrimidine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1550482A JPS58134082A (en) | 1982-02-04 | 1982-02-04 | Preparation of 2-alkyl-4-amino-5-formylpyrimidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1550482A JPS58134082A (en) | 1982-02-04 | 1982-02-04 | Preparation of 2-alkyl-4-amino-5-formylpyrimidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58134082A JPS58134082A (en) | 1983-08-10 |
| JPS626707B2 true JPS626707B2 (en) | 1987-02-13 |
Family
ID=11890633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1550482A Granted JPS58134082A (en) | 1982-02-04 | 1982-02-04 | Preparation of 2-alkyl-4-amino-5-formylpyrimidine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58134082A (en) |
-
1982
- 1982-02-04 JP JP1550482A patent/JPS58134082A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58134082A (en) | 1983-08-10 |
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