CN109265457A - A kind of new method using oxidation aromatisation building pyridopyrimidine dione skeleton - Google Patents

A kind of new method using oxidation aromatisation building pyridopyrimidine dione skeleton Download PDF

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CN109265457A
CN109265457A CN201811310102.8A CN201811310102A CN109265457A CN 109265457 A CN109265457 A CN 109265457A CN 201811310102 A CN201811310102 A CN 201811310102A CN 109265457 A CN109265457 A CN 109265457A
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substituted
aryl
pyrimidine
diketone
preparation
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孙海鹰
高歌
马宗辉
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China Pharmaceutical University
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China Pharmaceutical University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

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  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates to a kind of new methods using oxidation aromatisation building pyridopyrimidine dione skeleton.

Description

A kind of new method using oxidation aromatisation building pyridopyrimidine dione skeleton
Technical field
The present invention relates to a kind of new methods using oxidation aromatisation building pyridopyrimidine dione skeleton.
Background technique
When aryl and hybar X are a kind of new drug MOLECULE DESIGNs through frequently with skeleton, the compound tool with the skeleton There is extensive bioactivity and be widely used in new drug development, such as such compound is in a variety of GPCR regulators, novel Application in the research and development of PARP inhibitor etc. all has been reported.Pyridopyrimidine dione is the important composition portion of such compound Point, but the synthetic method report at present in document about pyridopyrimidine dione skeleton is fewer, and main method has the following two kinds: (1) cyclization is carried out with the condensing agents such as o-aminopyridine amide and triphosgene, CDI direct polycondensation；(2) o-aminopyridine formic acid esters is used Reacted with isocyanates, then under alkaline condition cyclization (J.Org.Chem.1987,52,616-622； ACS Med.Chem.Lett, 2016,7,547-548).Substituent group in these methods on nitrogen directly affects the efficiency of cyclization, therefore not Conducive to the building for carrying out compound library.
We devise a kind of new side by oxidative dehydrogenation aromatisation pyridine synthesis and hybar X skeleton in the present invention Method will have the compound library of pyridopyrimidine dione skeleton using this method building later, and be used for later new drug In development project.
Summary of the invention
The present invention provides the synthetic methods of the pyridopyrimidine dione class compound as shown in Formula II and formula IV:
Wherein R1、R5For C1-C10Linear chain or branched chain hydro carbons (wherein one or more methylene can by hetero atom, replace Or replaced non-substituted aryl, substituted or non-substituted heterocyclic aryl), the non-substituted or cyclic annular hydro carbons of 3~10 carbon that replaces (wherein one or more methylene or methine can be by the hetero atoms such as O, N, S, substituted or non-substituted aryl, substitutions or non- Replaced substituted heterocyclic aryl), it is non-substituted or replace aryl, it is non-substituted or replace heterocyclic aryl；R2For C1-C10It is straight (wherein one or more methylene or methine can be by hetero atom, substituted or non-substituted aryl, substitutions for chain or branch hydro carbons Or replaced non-substituted heterocyclic aryl), it is non-substituted or replace 3~10 carbon cyclic annular hydro carbons (wherein one or more methylenes Base or methine can be replaced hetero atom, substituted or non-substituted aryl, substituted or non-substituted heterocyclic aryls)；R3、R4 For hydrogen atom, C1-C10Linear chain or branched chain hydro carbons (wherein one or more methylene or methine can by hetero atom, replace Or replaced non-substituted aryl, substituted or non-substituted heterocyclic aryl), the non-substituted or cyclic annular hydro carbons of 3~10 carbon that replaces (wherein one or more methylene or methine can be by hetero atoms, substituted or non-substituted aryl, substituted or non-substituted miscellaneous Replaced cyclophane base), it is non-substituted or replace aryl, it is non-substituted or replace heterocyclic aryl.
Specific embodiment
Universal synthesis method
Compound representated by 1 equivalent formula I or formula III is dissolved in the in the mixed solvent of suitable acetonitrile and water, is divided at normal temperature The ammonium ceric nitrate that 1-5 equivalent is added is criticized, is stirred at room temperature to TLC display reaction and is basically completed, it is water-soluble that saturated sodium sulfite is added Liquid is quenched, evaporating solvent under reduced pressure, obtains product representated by Formula II or formula IV through extraction, concentration, column chromatographic purifying, yield: 40%-90%.
The contents of the present invention are illustrated below by embodiment.In the present invention, embodiments discussed below is in order to more preferable Elaboration the present invention, be not for limiting the scope of the invention.
Embodiment 1
Simultaneously [3,4-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) preparation of 1,3- lutidines
By 1,3- dimethyl -2,4- dioxo -1,3,4,5,7,8- hexahydropyridines simultaneously [4,3-d] pyrimidine -6 (2H)-carboxylic acid The tert-butyl ester (3) (100 mg, 0.339mmol), ammonium ceric nitrate (928mg, 1.69mmol) are dissolved in 3.7ml mixed solvent (acetonitrile: water =30: 7) in, 3h is stirred at room temperature, TLC display reaction is basically completed, saturated aqueous sodium sulfite is added and is quenched, removes under reduced pressure Solvent obtains white solid (46mg), yield: 66%-85% through column chromatographic purifying.mp.202-204℃；1H NMR (300MHz, Chloroform-d) δ 9.21 (s, 1H), 8.60 (d, J=5.1 Hz, 1H), 7.67 (d, J=5.0Hz, 1H), 3.32 (s, 3H), 2.79 (s, 3H)13C NMR (75MHz, Chloroform-d) δ 160.27,151.09,150.85,149.70,140.29, 108.77,108.26,30.99,28.71. MS (ESI) m/z:192.2 [M+H]+。
Embodiment 2
Simultaneously [4,3-d] pyrimidine-2,4 (1H, 3H)-diketone (I-2) preparation of 3- methyl-1-ethylpyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) Preparation1H NMR (300MHz, Chloroform-d) δ 9.21 (s, 1H), 8.60 (d, J=5.1Hz, 1H), 7.66 (d, J= 5.0Hz, 1H), 3.32 (s, 3H), 2.97 (q, J=8.0Hz, 2H), 1.40 (t, J=8.0Hz, 3H)13C NMR (75MHz, Chloroform-d) 160.27 δ, 151.28,150.98,148.86,139.61,109.96,107.01,38.44,28.58, 12.82.MS (ESI) m/z:206.2 [M+H]+。
Embodiment 3
Simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-3) preparation of 1- methyl -3-ethylpyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey.1H NMR (300MHz, Chloroform-d) δ 9.21 (s, 1H), 8.60 (d, J=5.1Hz, 1H), 7.67 (d, J =5.1Hz, 1H), 3.69 (q, J=8.0Hz, 2H), 2.79 (s, 3H), 1.18 (t, J=8.0Hz, 3H)；13C NMR (75MHz, Chloroform-d) 162.02 δ, 150.89,149.56,148.21,140.45,109.02,108.27,33.34,31.06, 13.31.MS (ESI) m/z:206.2 [M+H]+。。
Embodiment 4
Simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-4) preparation of 1- methyl -3- isopropyl pyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey.1H NMR (300MHz, Chloroform-d) δ 9.22 (s, 1H), 8.60 (d, J=5.0Hz, 1H), 7.67 (d, J =4.9Hz, 1H), 4.99 (m, 1H), 2.79 (s, 3H), 1.43 (d, J=6.8Hz, 6H)；13C NMR (75MHz, Chloroform-d) 161.58 δ, 151.26,150.96,149.44,140.65,109.31,108.28,47.03,30.99, 19.61.MS (ESI) m/z:220.2 [M+H]+。
Embodiment 5
Simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-5) preparation of 1- methyl -3- benzyl pyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey.1H NMR (300MHz, Chloroform-d) δ 9.21 (s, 1H), 8.58 (d, J=5.0Hz, 1H), 7.84 (d, J =5.1Hz, 1H), 7.49 (ddd, J=7.1,2.2,1.0Hz, 2H), 7.34-7.22 (m, 3H), 5.24 (s, 2H), 2.79 (s, 3H)；13C NMR (75MHz, Chloroform-d) δ 161.86,150.89,150.43,149.56,140.45,135.08, 129.40,128.54,127.64,109.02,108.27,44.96,31.06.MS (ESI) m/z:268.3 [M+H]+。
Embodiment 6
Simultaneously [4,3-d] pyrimidine-2,4 (1H, 3H)-diketone (I-6) preparation of 3- methyl-1-isopropyl pyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey.1H NMR (300MHz, Chloroform-d) δ 9.22 (s, 1H), 8.60 (d, J=5.0Hz, 1H), 7.63 (d, J =5.0Hz, 1H), 4.49 (m, 1H), 3.32 (s, 3H), 1.65 (d, J=6.8Hz, 6H)13C NMR (75MHz, Chloroform-d) 160.27 δ, 154.43,151.78,149.69,140.74,110.39,105.87,48.95,27.35, 19.56.MS (ESI) m/z:220.2 [M+H]+。
Embodiment 7
Simultaneously [4,3-d] pyrimidine-2,4 (1H, 3H)-diketone (I-7) preparation of 3- methyl-1-benzyl pyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey.1H NMR (300MHz, Chloroform-d) δ 9.20 (s, 1H), 8.56 (d, J=5.1Hz, 1H), 7.95 (d, J =5.1Hz, 1H), 7.32-7.28 (m, 2H), 7.26 (dt, J=7.3,1.5Hz, 3H), 4.64 (d, J=1.1Hz, 2H), 3.37 (s, 3H)13C NMR (75MHz, Chloroform-d) δ 160.27,151.62,151.43,149.64,139.38, 136.82,128.54,127.63,109.97,107.37,50.00,28.58.MS (ESI) m/z:268.3 [M+H]+。
Embodiment 8
Simultaneously [3,4-d] pyrimidine -2,4 (1H, 3H)-diketone (I-8) preparation of 1,3- lutidines
] concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey.MS (ESI) m/z:192.2 [M+H]+。
Embodiment 9
Simultaneously [3,4-d] pyrimidine-2,4 (1H, 3H)-diketone (I-9) preparation of 3- methyl-1-ethylpyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey.MS (ESI) m/z:206.2 [M+H]+。。
Embodiment 10
Simultaneously [3,4-d] pyrimidine -2,4 (1H, 3H)-diketone (I-10) preparation of 1- methyl -3-ethylpyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey.MS (ESI) m/z:206.2 [M+H]+。。
Embodiment 11
Simultaneously [3,4-d] pyrimidine -2,4 (1H, 3H)-diketone (I-11) preparation of 1- methyl -3- isopropyl pyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey.MS (ESI) m/z:220.2 [M+H]+。
Embodiment 12
Simultaneously [3,4-d] pyrimidine -2,4 (1H, 3H)-diketone (I-12) preparation of 1- methyl -3- benzyl pyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey.MS (ESI) m/z:267.3 [M+H]+。
Embodiment 13
Simultaneously [3,4-d] pyrimidine-2,4 (1H, 3H)-diketone (I-13) preparation of 3- methyl-1-isopropyl pyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey, MS (ESI) m/z:220.2 [M+H]+。
Embodiment 14
Simultaneously [3,4-d] pyrimidine-2,4 (1H, 3H)-diketone (I-14) preparation of 3- methyl-1-benzyl pyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey, MS (ESI) m/z:268.3 [M+H]+。
Embodiment 15
The preparation of 1,3,5- trimethyl-pyrido [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-15)
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey, MS (ESI) m/z:206.2 [M+H]+。
Embodiment 16
The preparation of 1,3,7- trimethyl-pyrido [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-15)
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey, MS (ESI) m/z:206.2 [M+H]+。
Embodiment 17
Simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-17) preparation of 1- ethyl -3-ethylpyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey, MS (ESI) m/z:220.2 [M+H]+。
Embodiment 18
Simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-17) preparation of 1- ethyl -3- isopropyl pyridine
Concrete operations reference compound 1,3- lutidines simultaneously [4,3-d] pyrimidine -2,4 (1H, 3H)-diketone (I-1) mistake The preparation of journey, MS (ESI) m/z:234.3 [M+H]+。
Embodiment 18
Synthetic method bibliography the Marion C.Lanier, Miklos of part of compounds representated by Formulas I or formula III Feher, Neil J. Ashweek, et al. [J] .Bioorganic&Medicinal Chemistry, 2007,15:5590- 5603。

Claims (1)

1. the synthetic method for the pyridopyrimidine dione class compound being shown below:
Wherein R1、R5For C1-C10Linear chain or branched chain hydro carbons (wherein one or more methylene can be by hetero atom, substitution or non- Replaced substituted aryl, substituted or non-substituted heterocyclic aryl), the non-substituted or cyclic annular hydro carbons of 3~10 carbon that replaces (wherein One or more methylene or methine can be by hetero atoms such as O, N, S, substituted or non-substituted aryl, substituted or non-substituted Replaced heterocyclic aryl), it is non-substituted or replace aryl, it is non-substituted or replace heterocyclic aryl；R2For C1-C10Straight chain or branch (wherein one or more methylene or methine by hetero atom, substituted or non-substituted aryl, substitution or non-can take catenanes Replaced the heterocyclic aryl in generation), (wherein one or more methylene are secondary for the non-substituted or cyclic annular hydro carbons of 3~10 carbon that replaces Methyl can be replaced hetero atom, substituted or non-substituted aryl, substituted or non-substituted heterocyclic aryl)；R3、R4For hydrogen original Son, C1-C10Linear chain or branched chain hydro carbons (wherein one or more methylene or methine by hetero atom, substitution or non-can take Replaced the aryl in generation, substituted or non-substituted heterocyclic aryl), the non-substituted or cyclic annular hydro carbons (wherein one of 3~10 carbon that replaces A or multiple methylene or methine can be by hetero atom, substituted or non-substituted aryl, substituted or non-substituted heterocyclic aryls It is replaced), it is non-substituted or replace aryl, it is non-substituted or replace heterocyclic aryl.
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US11608344B2 (en) 2020-05-04 2023-03-21 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells 2 agonists and methods of use
US11718617B2 (en) 2020-05-04 2023-08-08 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells2 agonists and methods of use

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11608344B2 (en) 2020-05-04 2023-03-21 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells 2 agonists and methods of use
US11718617B2 (en) 2020-05-04 2023-08-08 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells2 agonists and methods of use
US11884675B2 (en) 2020-05-04 2024-01-30 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells 2 agonists and methods of use
US11912711B2 (en) 2020-05-04 2024-02-27 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells 2 agonists and methods of use

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Application publication date: 20190125