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【结 构 式】

【药物名称】Wy-14643

【化学名称】2-[4-Chloro-6-(2,3-dimethylphenylamino)pyrimidin-2-ylsulfanyl]acetic acid

【CA登记号】50892-23-4

【 分 子 式 】C14H14ClN3O2S

【 分 子 量 】323.80358

【开发单位】Wyeth Pharmaceuticals (Originator)

【药理作用】Antidiabetic Drugs, ENDOCRINE DRUGS, Type 2 Diabetes Mellitus, Agents for, PPARalpha Agonists

合成路线1

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
Extended Information