Sodium hydride → 4-chloro-2-methylmercapto-7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

関与物質

役割	名称	HCID	仕込み量
反応物	Sodium hydride	HCID 24758	—
反応物	4-chloro-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine	HCID 5324414	—
反応物	(2R,3R,4S,5R)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)-5-chlorotetrahydrofuran	HCID 10895454	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	4-chloro-2-methylmercapto-7-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine	HCID 13277177	—

反応条件

温度	50 °C

反応手順

A suspension of 3.1 g sodium hydride, 25.9 g of 4-chloro-2-methylmercapto-7H-pyrrolo[2,3-d]pyrimidine, and 250 ml of dry dimethylformamide (DMF) is stirred at 50° C. for 0.5 hour, cooled, and added to 62.8 g of 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride. The solution is stirred at ambient temperature for 15 hours, concentrated in vacuo, and distributed between a mixture of ethyl acetate and water. Chromatrography of the dried (MgSO4) layer over silica gel with 4:1 toluene-ethyl acetate provides 76 g of yellow, syrupy 4-chloro-2-methylmercapto-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US04352795
出典データセット	uspto-grants-1982_10
ORD ID	ord-87de7956b3e04267aa13610b6920b1b3
出典メモ	uspto-grants-1982_10