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【结 构 式】 
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【分子编号】15227 【品名】4-chloropyrido[2,3-d]pyrimidin-2-yl methyl sulfide; 4-chloro-2-(methylsulfanyl)pyrido[2,3-d]pyrimidine 【CA登记号】 |
【 分 子 式 】C8H6ClN3S 【 分 子 量 】211.67456 【元素组成】C 45.39% H 2.86% Cl 16.75% N 19.85% S 15.15% |
合成路线1
该中间体在本合成路线中的序号：(IV)The synthesis of MD-39-AM (V) was carried out as follows: From 2-chloronicotinic acid (as its acyl chloride) (I) and thiourea in triethylamine (1:1:2), compound (II) was obtained. However, in order to avoid the substitution of 2-Cl by sulfur, 2-methylisothiourea was used. By boiling a solution of (II) in dimethylformamide (DMF) for 15 min, (III) (87%) was obtained. Reaction of (III) with phosphorous oxychloride gave 4-chloro-2-(methylthio)pyrido[2,3-d]pyrimidine (IV) (90%). By reacting (IV) with aniline in ethanol, MD-39-AM was obtained.
| 【1】 Martinez-Merino, V.; Ochoa, M.C.; Fernandez, F.J.; Artigas, P.; Monge, A.; Bellver, C.; Sanmartin, C.; Fernandez-Alvarez, E.; 2-Arylamino-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidines: Synthesis and diuretic activity. Eur J Med Chem 1989, 24, 209. |
| 【2】 Martinez-Merino, V.; Monge, A.; Sanmartin, C.; MD-39-AM. Drugs Fut 1992, 17, 2, 107. |
| 【3】 Ochoa, M.C.; Fernández, F.J.; Sanmartín, C.; Monge, A.; Martínez-Merino, V.; Bellver, C.; Artigas, P.; Diuretic and hypotensive activities of 4-anilino derivatives of 2-methylthiopyrido[2,3-d]pyrimidines. Arzneim-Forsch Drug Res 1990, 40, 11, 1230-3. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10272 | [[Amino(imino)methyl]sulfanyl]methane | 2986-19-8 | C2H6N2S | 详情 | 详情 | |
| (I) | 15224 | 2-chloronicotinoyl chloride | 49609-84-9 | C6H3Cl2NO | 详情 | 详情 |
| (II) | 15225 | 2-chloro-3-([[imino(methylsulfanyl)methyl]amino]carbonyl)pyridine | C8H8ClN3OS | 详情 | 详情 | |
| (III) | 15226 | 2-(methylsulfanyl)pyrido[2,3-d]pyrimidin-4-ol | C8H7N3OS | 详情 | 详情 | |
| (IV) | 15227 | 4-chloropyrido[2,3-d]pyrimidin-2-yl methyl sulfide; 4-chloro-2-(methylsulfanyl)pyrido[2,3-d]pyrimidine | C8H6ClN3S | 详情 | 详情 |