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【结 构 式】

【分子编号】60410

【品名】4-hydroxy-6-(3-methoxyphenyl)-2-(methylsulfanyl)-5-pyrimidinecarbonitrile

【CA登记号】

【 分 子 式 】C13H11N3O2S

【 分 子 量 】273.31536

【元素组成】C 57.13% H 4.06% N 15.37% O 11.71% S 11.73%

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:(IV)

The condensation between 3-methoxybenzaldehyde (I), S-methylisothiourea (II) and ethyl cyanoacetate (III) in the presence of K2CO3 in hot EtOH leads to pyrimidine (IV). Subsequent chlorination of (IV) by means of POCl3 and dimethylaniline furnishes the 6-chloropyrimidine (V). Reaction of (V) with ethyl mercaptoacetate (VI) and potassium tert-butoxide gives rise to the thienopyrimidine (VII). The ethyl ester group of (VII) is then hydrolyzed to the carboxylic acid (VIII) employing LiOH. Finally, coupling of acid (VIII) with tert-butylamine by means of TBTU produces the target N-tert-butyl amide

1 Adang, A.E.P.; Gerritsma, G.G.; Van Straten, N.C.R. (Akzo Nobel N.V.); Bicyclic heteroaromatic cpds. useful as LH agonists. EP 1171443; JP 2002541259; US 6569863; WO 0061586 .
2 Timmers, C.M.; Karstens, W.F.J. (Akzo Nobel N.V.); Bicyclic heteroaromatic cpds.. WO 0224703 .
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) 20589 3-methoxybenzaldehyde; m-Anisaldehyde 591-31-1 C8H8O2 详情 详情
(II) 10272 [[Amino(imino)methyl]sulfanyl]methane 2986-19-8 C2H6N2S 详情 详情
(III) 11877 Cyanoacetic acid ethyl ester; Ethyl 2-cyanoacetate; Ethyl cyanoacetate; Ethyl isocyanacetate 105-56-6 C5H7NO2 详情 详情
(IV) 60410 4-hydroxy-6-(3-methoxyphenyl)-2-(methylsulfanyl)-5-pyrimidinecarbonitrile C13H11N3O2S 详情 详情
(V) 60411 4-chloro-6-(3-methoxyphenyl)-2-(methylsulfanyl)-5-pyrimidinecarbonitrile C13H10ClN3OS 详情 详情
(VI) 23995 ethyl 2-sulfanylacetate 2713-34-0 C4H8O2S 详情 详情
(VII) 60412 ethyl 5-amino-4-(3-methoxyphenyl)-2-(methylsulfanyl)thieno[2,3-d]pyrimidine-6-carboxylate C17H17N3O3S2 详情 详情
(VIII) 60413 5-amino-4-(3-methoxyphenyl)-2-(methylsulfanyl)thieno[2,3-d]pyrimidine-6-carboxylic acid C15H13N3O3S2 详情 详情
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