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【结 构 式】

【分子编号】29072

【品名】2-chloro-3-methyl-5-nitropyridine

【CA登记号】

【 分 子 式 】C6H5ClN2O2

【 分 子 量 】172.57068

【元素组成】C 41.76% H 2.92% Cl 20.54% N 16.23% O 18.54%

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:(II)

The condensation of diethyl 2-(2-cyanoethyl)malonate (I) with 2-chloro-3-methyl-5-nitropyridine (II) by means of NaH in refluxing THF gives 4-(3-methyl-5-nitropyrid-2-yl)-4,4-bis(ethoxycarbonyl)butyronitrile (III), which is decarboxylated with NaOH in ethanol water yielding 4-(3-methyl-5-nitropyrid-2-yl)butyronitrile (IV). The reduction of (IV) with H2 over Pd/C in ethanol affords 4-(5-amino-3-methylpyrid-2-yl)butyronitrile (V), which is reduced further with LiAlH4 in ether-THF giving 5-amino-2-(4-aminobutyl)-3-methylpyridine (VI). The Sandmeyer reaction of (VI) with NaNO2, HBr and Cu2Br2 yields 5-bromo-2-(4-aminobutyl)-3-methylpyridine (VII), which is finally condensed with 2-nitroamino-5-(6-methylpyrid-2-ylmethyl)-4-pyrimidone (VIII) in refluxing pyridine.

1 Sach, G.S. (SmithKline Beecham plc); Histamine H1-antagonists. DD 202291; EP 0068833; EP 0068834; JP 58008079; JP 61233616; JP 61233670; US 4444772; US 4486434; US 4535163; US 4584381 .
2 Serradell, M.N.; Castaner, J.; SKF-93944. Drugs Fut 1985, 10, 3, 209.
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) 22941 diethyl 2-(2-cyanoethyl)malonate 17216-62-5 C10H15NO4 详情 详情
(II) 29072 2-chloro-3-methyl-5-nitropyridine C6H5ClN2O2 详情 详情
(III) 29073 Diethyl 2-(2-cyanoethyl)-2-(3-methyl-5-nitro-2-pyridinyl)malonate C16H19N3O6 详情 详情
(IV) 29074 4-(3-methyl-5-nitro-2-pyridinyl)butanenitrile C10H11N3O2 详情 详情
(V) 29075 4-(5-amino-3-methyl-2-pyridinyl)butanenitrile C10H13N3 详情 详情
(VI) 29076 6-(4-aminobutyl)-5-methyl-3-pyridinamine C10H17N3 详情 详情
(VII) 29077 4-(5-bromo-3-methyl-2-pyridinyl)-1-butanamine C10H15BrN2 详情 详情
(VIII) 22953 5-(6-Methylpyridin-3-ylmethyl)-2-(nitroamino)pyrimidin-4(1H)-one C11H11N5O3 详情 详情
Extended Information