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

【结 构 式】

【分子编号】48624

【品名】ethyl 1-(2,2-diethoxyethyl)-2-(3-methoxyphenyl)-6-oxo-1,6-dihydro-5-pyrimidinecarboxylate

【CA登记号】

【 分 子 式 】C20H26N2O6

【 分 子 量 】390.43632

【元素组成】C 61.53% H 6.71% N 7.17% O 24.59%

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:(VI)

3-Methoxybenzonitrile (I) was converted to the corresponding imidate (II) by treatment with ethanolic HCl. Condensation of (II) with aminoacetaldehyde diethyl acetal (III) gave amidine (IV), which was cyclized with diethyl ethoxymethylenemalonate (V) in refluxing ethanol to yield the pyrimidinone (VI). Hydrolysis of the ethyl ester function of (VI) by treatment with LiI in hot pyridine provided acid (VII). This was subjected to a Curtius rearrangement with diphenylphosphoryl azide, and the intermediate isocyanate was condensed with benzyl alcohol to produce the benzyl carbamate (VIII). Acid hydrolysis of the diethyl acetal group of (VIII), followed by oxidation of the resulting aldehyde with sodium chlorite, furnished the carboxylic acid (IX).

1 Akahoshi, F.; Ashimori, A.; Yoshimura, T.; Eda, M.; Sakashita, H.; Nakajima, M.; Imada, T. (Welfide Corporation); Novel heterocyclic amide cpds. and medicinal uses thereof. EP 0940400; US 6080738; WO 9818794 .
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) 36250 3-methoxybenzonitrile 1527-89-5 C8H7NO 详情 详情
(II) 34363 ethyl 3-methoxybenzenecarboximidoate C10H13NO2 详情 详情
(III) 10331 2,2-Diethoxy-1-ethanamine; 2,2-Diethoxyethylamine; Aminoacetaldehyde diethyl acetal 645-36-3 C6H15NO2 详情 详情
(IV) 48623 N-(2,2-diethoxyethyl)-3-methoxybenzenecarboximidamide C14H22N2O3 详情 详情
(V) 14088 Diethyl ethoxymethylenemalonate; Diethyl 2-(ethoxymethylene)malonate 87-13-8 C10H16O5 详情 详情
(VI) 48624 ethyl 1-(2,2-diethoxyethyl)-2-(3-methoxyphenyl)-6-oxo-1,6-dihydro-5-pyrimidinecarboxylate C20H26N2O6 详情 详情
(VII) 48625 1-(2,2-diethoxyethyl)-2-(3-methoxyphenyl)-6-oxo-1,6-dihydro-5-pyrimidinecarboxylic acid C18H22N2O6 详情 详情
(VIII) 48626 benzyl 1-(2,2-diethoxyethyl)-2-(3-methoxyphenyl)-6-oxo-1,6-dihydro-5-pyrimidinylcarbamate C25H29N3O6 详情 详情
(IX) 48627 2-[5-[[(benzyloxy)carbonyl]amino]-2-(3-methoxyphenyl)-6-oxo-1(6H)-pyrimidinyl]acetic acid C21H19N3O6 详情 详情
Extended Information