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【结 构 式】

【分子编号】31549

【品名】N-[2-[(2,2-dimethylpropanoyl)amino]-6-[(E)-2-phenylethenyl]pyrido[2,3-d]pyrimidin-4-yl]-2,2-dimethylpropanamide

【CA登记号】

【 分 子 式 】C25H29N5O2

【 分 子 量 】431.53776

【元素组成】C 69.58% H 6.77% N 16.23% O 7.42%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XI)

In an alternative synthesis, 2,4,6-triaminopyrimidine (VI) was condensed with bromomalonaldehyde (VII) under acidic conditions to give pyridopyrimidine (VIII), which was protected with pivaloyl anhydride in pyridine, yielding the bispivaloylamide (IX). Palladium-catalyzed Heck coupling of (IX) with styrene (X) afforded (XI). Subsequent ozonolysis of the styryl derivative (XI), followed by reductive workup with dimethyl sulfide gave aldehyde (XII). Reduction of (XII) to the corresponding alcohol with NaBH4, followed by bromination with PPh3 and Br2 provided bromide (XIII). The N-methyl aniline (XIV) was synthesized by direct alkylation of 3,4,5-trimethoxyaniline (IV) with methyl iodide. Nucleophilic displacement of the bromide (XIII) with aniline (XIV) afforded the tertiary amine (XV). The pivaloyl protecting groups of (XV) were finally removed by treatment with methanolic NaOMe.

1 Gangjee, A.; et al.; Synthesis and dihydrofolate reductase inhibitory activities of 2,4-diamino-5-deaza and 2,4-diamino-5, 10-dideaza lipophilic antifolates. J Med Chem 1997, 40, 4, 470.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 31545 3,4,5-trimethoxyaniline; 3,4,5-trimethoxyphenylamine;3,4,5-Trimethoxybenzenamine;[3,4,5-Tris(methyloxy)phenyl]amine 24313-88-0 C9H13NO3 详情 详情
(VI) 28977 2,6-diamino-4-pyrimidinylamine 1004-38-2 C4H7N5 详情 详情
(VII) 14278 2-Bromomalonaldehyde C3H3BrO2 详情 详情
(VIII) 31547 6-bromopyrido[2,3-d]pyrimidine-2,4-diamine; 2-amino-6-bromopyrido[2,3-d]pyrimidin-4-ylamine C7H6BrN5 详情 详情
(IX) 31548 N-[6-bromo-2-[(2,2-dimethylpropanoyl)amino]pyrido[2,3-d]pyrimidin-4-yl]-2,2-dimethylpropanamide C17H22BrN5O2 详情 详情
(X) 19649 1-vinylbenzene 100-42-5 C8H8 详情 详情
(XI) 31549 N-[2-[(2,2-dimethylpropanoyl)amino]-6-[(E)-2-phenylethenyl]pyrido[2,3-d]pyrimidin-4-yl]-2,2-dimethylpropanamide C25H29N5O2 详情 详情
(XII) 31550 N-[2-[(2,2-dimethylpropanoyl)amino]-6-formylpyrido[2,3-d]pyrimidin-4-yl]-2,2-dimethylpropanamide C18H23N5O3 详情 详情
(XIII) 31554 3-bromo-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-5-one C11H11BrO 详情 详情
(XIV) 31552 3,4,5-trimethoxy-N-methylaniline; N-methyl-N-(3,4,5-trimethoxyphenyl)amine C10H15NO3 详情 详情
(XV) 31553 N-(2-[(2,2-dimethylpropanoyl)amino]-6-[[3,4,5-trimethoxy(methyl)anilino]methyl]pyrido[2,3-d]pyrimidin-4-yl)-2,2-dimethylpropanamide C28H38N6O5 详情 详情
Extended Information