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【结 构 式】 
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【分子编号】54310 【品名】6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ol 【CA登记号】n/a |
【 分 子 式 】C13H11N3O2 【 分 子 量 】241.24936 【元素组成】C 64.72% H 4.6% N 17.42% O 13.26% |
合成路线1
该中间体在本合成路线中的序号：(IV)The cyclization of 4-methoxyphenacyl bromide (I) with 2-amidinoacetic acid ethyl ester (II) by means of sodium ethoxide in ethanol gives 2-amino-5-(4-methoxyphenyl)-1H-pyrrole-3-carboxylic acid ethyl ester (III), which is cyclized with formamide in DMF at 150 C to yield the pyrrolopyrimidine (IV). The reaction of the OH group of (IV) with POCl3 at 150 C affords the corresponding chloro derivative (V), which is condensed with 1(R)-phenylethylamine (VI) in refluxing butanol to provide the adduct (VII). Finally, this compound is demethylated by means of BBr3 in dichloromethane to furnish the target pyrrolopyrimidine.
| 【1】 Traxler, P.; Bold, G.; Brill, W.K.-D.; Frei, J. (Novartis AG); Pyrrolopyrimidines and processes for the preparation thereof. EP 0836605; JP 1999508570; US 6140332; WO 9702266 . |
| 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) | 21991 | 2-Methoxyphenacyl bromide; 2-bromo-1-(4-methoxyphenyl)-1-ethanone | 2632-13-5 | C9H9BrO2 | 详情 | 详情 |
| (II) | 54308 | ethyl 3-amino-3-iminopropanoate | 50551-10-5 | C5H10N2O2 | 详情 | 详情 |
| (III) | 54309 | ethyl 2-amino-5-(4-methoxyphenyl)-1H-pyrrole-3-carboxylate | n/a | C14H16N2O3 | 详情 | 详情 |
| (IV) | 54310 | 6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ol | n/a | C13H11N3O2 | 详情 | 详情 |
| (V) | 54311 | 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl methyl ether; 4-chloro-6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidine | n/a | C13H10ClN3O | 详情 | 详情 |
| (VI) | 10039 | (1R)-1-Phenylethylamine; (1R)-1-Phenyl-1-ethanamine.; L-alpha-Phenylethylamine | 3886-69-9 | C8H11N | 详情 | 详情 |
| (VII) | 54312 | N-[6-(4-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-N-[(1R)-1-phenylethyl]amine; 6-(4-methoxyphenyl)-N-[(1R)-1-phenylethyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine | n/a | C21H20N4O | 详情 | 详情 |