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【结 构 式】 
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【分子编号】61117 【品名】ethyl 2-[(4,6-dichloro-2-pyrimidinyl)sulfanyl]acetate 【CA登记号】 |
【 分 子 式 】C8H8Cl2N2O2S 【 分 子 量 】267.1352 【元素组成】C 35.97% H 3.02% Cl 26.54% N 10.49% O 11.98% S 12% |
合成路线1
该中间体在本合成路线中的序号：(IV)The reaction of 2-thiobarbituric acid (I) with ethyl bromoacetate (II) by means of NaHCO3 in ethanol - water gives ethyl-(4,6-dihydroxy-2-pyrimidinylthio)acetate (III), which by halogenation with POCl3 and N,N-diethylaniline yields ethyl (4,6-dichloro-2-pyrimidinylthio)acetate (IV). The condensation of (IV) with 2,3-dimethylaniline (V) by means of Na2CO3 in refluxing ethanol affords ethyl [4-chloro-6-(2,3-xylidino)-2-pyrimidinylthio]acetate (VI), which is finally hydrolyzed with Na2CO3 in refluxing ethanol. Description.- Crystals, m.p. 146-51 C; Na salt, m.p. 183 C (decomp.).
| 【1】 Castaner, J.; Paton, D.M.; Wy - 14643. Drugs Fut 1978, 3, 5, 404. |
| 【2】 Santilli, A.A.; et al.; Natural product resveratrol: Novel sensitizer of tumor cells for TRAIL- or cytotoxic drug-induced apoptosis by cell cycle-mediated survivin depletion. Experientia 1974, 30, 10, 1110. |
| 【3】 Santilli, A.A.; et al.; US 3940394 . |
| 【4】 Santilli, A.A.; et al. (American Home Products Corp.); US 3910910 . |
| 【5】 Santilli, A.A.; et al. (American Home Products Corp.); CA 967571; DE 2314160; FR 2182917; GB 1413892; US 3814761; US 3876789; US 3896129; ZA 7301526 . |
| 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) | 25623 | 2-Thiobarbituric acid; 4,5-Dihydroxy-2-mercaptopyrimidine; 2-sulfanyl-4,6-pyrimidinediol | 504-17-6 | C4H4N2O2S | 详情 | 详情 |
| (II) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (III) | 61116 | ethyl 2-[(4,6-dihydroxy-2-pyrimidinyl)sulfanyl]acetate | C8H10N2O4S | 详情 | 详情 | |
| (IV) | 61117 | ethyl 2-[(4,6-dichloro-2-pyrimidinyl)sulfanyl]acetate | C8H8Cl2N2O2S | 详情 | 详情 | |
| (V) | 23025 | 2,3-Dimethylphenylamine; 2,3-Dimethylaniline; 2,3-Xylidine | 87-59-2 | C8H11N | 详情 | 详情 |
| (VI) | 61118 | ethyl 2-{[4-chloro-6-(2,3-dimethylanilino)-2-pyrimidinyl]sulfanyl}acetate | C16H18ClN3O2S | 详情 | 详情 |