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【结 构 式】 
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【分子编号】60413 【品名】5-amino-4-(3-methoxyphenyl)-2-(methylsulfanyl)thieno[2,3-d]pyrimidine-6-carboxylic acid 【CA登记号】 |
【 分 子 式 】C15H13N3O3S2 【 分 子 量 】347.41864 【元素组成】C 51.86% H 3.77% N 12.09% O 13.82% S 18.46% |
合成路线1
该中间体在本合成路线中的序号：(VIII)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 |