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 -Drug Synthesis Database

【结构式】

【分子编号】54311

【品名】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

【CA登记号】n/a

【分子式】C₁₃H₁₀ClN₃O

【分子量】259.69472

【元素组成】C 60.13% H 3.88% Cl 13.65% N 16.18% O 6.16%

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：(V)

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.

参考文献中间体

合成目标

【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

Extended Information