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【结 构 式】

【分子编号】36448

【品名】5-[(6-methyl-3-pyridinyl)methyl]-2-(methylsulfanyl)-4(3H)-pyrimidinone

【CA登记号】

【 分 子 式 】C12H13N3OS

【 分 子 量 】247.32084

【元素组成】C 58.28% H 5.3% N 16.99% O 6.47% S 12.97%

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:(IX)

The condensation of 6-methylpyridine-3-carboxaldehyde (I) with malonic acid (II) by means of piperidine in refluxing pyridine gives 3-(6-methyl-3-pyridyl)acrylic acid (III), which is esterified with ethanol and H2SO4 as usual to afford ethyl 3-(6-methyl-3-pyridyl)acrylate (IV). The reduction of (IV) with H2 over Pd/C in ethanol affords ethyl 3-(6-methyl-3-pyridyl)propionate (V), which is cyclized with ethyl formate (VI) and thiourea (VII) by means of Na in ether-ethanol yielding 5-(6-methyl-3-pyridylmethyl)-2-thiouracil (VIII). The methylation of (VIII) with methyl iodide and NaOH in hot water gives 5-(6-methyl-3-pyridyl-methyl)-2-methylthio-4-pyrimidone (IX), which is finally condensed with 2-[(5-dimethylaminomethylfuran-2-yl)methylthio]ethylamine (X) in refluxing pyridine.

1 Brown, T.H.; Ife, R.J. (SmithKline Beecham plc); Pyrimidine compounds. DD 140252; EP 0003677; ES 477667; US 4234588; US 4649141 .
2 de Angelis, L.; Serradell, M.N.; Castaner, J.; Blancafort, P.; SKF-93,479. Drugs Fut 1982, 7, 3, 175.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 22949 6-methylnicotinaldehyde C7H7NO 详情 详情
(II) 12963 Malonic acid 141-82-2 C3H4O4 详情 详情
(III) 22950 (E)-3-(6-methyl-3-pyridinyl)-2-propenoic acid C9H9NO2 详情 详情
(IV) 36446 ethyl (E)-3-(6-methyl-3-pyridinyl)-2-propenoate C11H13NO2 详情 详情
(V) 22951 ethyl 3-(6-methyl-3-pyridinyl)propanoate C11H15NO2 详情 详情
(VI) 16602 ethyl formate 109-94-4 C3H6O2 详情 详情
(VII) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(VIII) 36447 5-[(6-methyl-3-pyridinyl)methyl]-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone C11H11N3OS 详情 详情
(IX) 36448 5-[(6-methyl-3-pyridinyl)methyl]-2-(methylsulfanyl)-4(3H)-pyrimidinone C12H13N3OS 详情 详情
(X) 13851 2-[([5-[(Dimethylamino)methyl]-2-furyl]methyl)sulfanyl]-1-ethanamine; N-[(5-[[(2-Aminoethyl)sulfanyl]methyl]-2-furyl)methyl]-N,N-dimethylamine C10H18N2OS 详情 详情
Extended Information