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【结 构 式】 
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【分子编号】22737 【品名】methyl 2-cyano-3,3-bis(methylsulfanyl)acrylate 【CA登记号】 |
【 分 子 式 】C7H9NO2S2 【 分 子 量 】203.286 【元素组成】C 41.36% H 4.46% N 6.89% O 15.74% S 31.55% |
合成路线1
该中间体在本合成路线中的序号：(II)The cyclization of acetamidine (I) with 2-cyano-3,3-bis(methylthio)-2-propenoic acid methyl ester (II) by means ot NaH in DMF gives 2-methyl-6-(methylthio)-4 oxo-1,4-dihydropyrimidine-5-carbonitrile (III), which is then condensed with 3-pyridylmethyl amine (IV) by refluxing in dimethoxyethane solution.
| 【1】 Bagli, J.F. (American Home Products Corp.); Amino-pyrimidine derivs.. EP 0130735; ES 8602694; JP 1985025974; US 4505910 . |
| 【2】 Prous, J.; Castaner, J.; Pelrinone hydrochloride. Drugs Fut 1988, 13, 8, 728. |
| 【3】 Bagli, J.; Bogri, T.; Palameta, B.; Rakhit, S.; Peseckis, S.; McQuillan, J.; Lee, D.K.; Chemistry and positive inotropic effect of pelrino. J Med Chem 1988, 31, 4, 814-23. |
| 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) | 15866 | ethanimidamide | C2H6N2 | 详情 | 详情 | |
| (II) | 22737 | methyl 2-cyano-3,3-bis(methylsulfanyl)acrylate | C7H9NO2S2 | 详情 | 详情 | |
| (III) | 22738 | 2-methyl-6-(methylsulfanyl)-4-oxo-1,4-dihydro-5-pyrimidinecarbonitrile | C7H7N3OS | 详情 | 详情 | |
| (IV) | 18731 | 3-pyridinylmethanamine; 3-pyridinylmethylamine | 3731-52-0 | C6H8N2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)The condensation of ethyl 2-cyano-3,3-dimethylthioacrylate (I) with S-methylisothiourea (II) in refluxing ethanol yielded pyrimidinone (V). Alternatively, the intermediate pyrimidinone (V) was obtained by condensation of 2-cyano-3,3-dimethylthioacrylamide (III) with anhydride (IV). Subsequent chlorination of (V) with refluxing phosphoryl chloride provided the title chloropyrimidine.
| 【1】 Upadyay, D.N.; Ram, V.J.; Shukla, P.K.; Raghywanshi, s.K.; Agarwal, N.; Suitably functionalised pyrimidines as potential antimycotic agents. Bioorg Med Chem Lett 2000, 10, 8, 703. |
| 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) | 22737 | methyl 2-cyano-3,3-bis(methylsulfanyl)acrylate | C7H9NO2S2 | 详情 | 详情 | |
| (II) | 10278 | 2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)acetyl chloride | 6780-38-7 | C10H6ClNO3 | 详情 | 详情 |
| (III) | 55361 | 2-cyano-3,3-bis(methylsulfanyl)acrylamide | C6H8N2OS2 | 详情 | 详情 | |
| (IV) | 55362 | C4H6O3S2 | 详情 | 详情 | ||
| (V) | 55363 | 2,4-bis(methylsulfanyl)-6-oxo-1,6-dihydro-5-pyrimidinecarbonitrile | C7H7N3OS2 | 详情 | 详情 |