• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】47911

【品名】5-[2-(trimethylsilyl)ethynyl]-2,4(1H,3H)-pyrimidinedione

【CA登记号】

【 分 子 式 】C9H12N2O2Si

【 分 子 量 】208.29206

【元素组成】C 51.9% H 5.81% N 13.45% O 15.36% Si 13.48%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(III)

This compound has been obtained by two similar ways: 1. The reaction of 5-iodouracil (I) with trimethylsilylacetylene (II) by means of PdCl2(PPh3)2 and CuI2 in TEA/DMF gives 5-(trimethylsilylethynyl)uracil (III), which is then desilylated with sodium methoxide or NaOH in methanol. 2. The reaction of 5-iodouracil (I) with POCl3 at 120 C catalyzed by N,N-diethylaniline gives 2,4-dichloro-5-iodopyrimidine (IV), which by reaction with NaOMe in methanol is converted into 2,4-dimethoxy-5-iodopyrimidine (V). The condensation of (V) with trimethylsilylacetylene by means of PdCl2(PPh3)2 and CuI2 in TEA/DMF yields 2,4-dimethoxy-5-(trimethylsilylethynyl)pyrimidine (VI), which is treated with NaI and Tms-Cl in refluxing acetonitrile to afford 5-(trimethylsilylethynyl)uracil (III).

1 Cooke, J.W.B.; et al.; Process research and development of a dihydropyrimidine dehydrogenase inactivator: Large-scale preparation of eniluracil using a Sonogashira coupling. Org Process Res Dev 2001, 5, 4, 383.
2 Spector, T.; Porter, D.J.T.; Rahim, S.G. (Glaxo Wellcome plc); Uracil reductase inactivators. EP 0550580; JP 1994504263; JP 1998045623; WO 9204901 .
3 Spector, T.; Porter, D.J.T.; Rahim, S.G. (Glaxo Wellcome plc); Enzyme inactivators. EP 0539442; EP 0711555; JP 1994502619; JP 2000297076; WO 9201452 .
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) 11867 5-Iodo-2,4(1H,3H)-pyrimidinedione 696-07-1 C4H3IN2O2 详情 详情
(II) 23897 ethynyl(trimethyl)silane;trimethylsilyl acetylene 1066-54-2 C5H10Si 详情 详情
(III) 47911 5-[2-(trimethylsilyl)ethynyl]-2,4(1H,3H)-pyrimidinedione C9H12N2O2Si 详情 详情
(IV) 11868 2,4-Dichloro-5-iodopyrimidine C4HCl2IN2 详情 详情
(V) 11869 5-Iodo-2-methoxy-4-pyrimidinyl methyl ether; 5-Iodo-2,4-dimethoxypyrimidine 52522-99-3 C6H7IN2O2 详情 详情
(VI) 47912 2,4-dimethoxy-5-[2-(trimethylsilyl)ethynyl]pyrimidine; 2-methoxy-5-[2-(trimethylsilyl)ethynyl]-4-pyrimidinyl methyl ether C11H16N2O2Si 详情 详情
Extended Information