【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% |
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 |