… . 118. Nonaqueous Diazotization of Aminopurine Derivatives. Convenient Access to 6-Halo-and 2, 6-Dihalopurine Nucleosides and 2'-Deoxynucleosides with Acyl or …

P Francom, MJ Robins

Index: Francom, Paula; Robins, Morris J. Journal of Organic Chemistry, 2003 , vol. 68, # 2 p. 666 - 669

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Citation Number: 39

Abstract

Treatment of 9-(2, 3, 5-tri-O-acetyl-β-d-ribofuranosyl)-2-amino-6-chloropurine (1) with TMS- Cl and benzyltriethylammonium nitrite (BTEA-NO2) in dichloromethane gave the crystalline 2, 6-dichloropurine nucleoside 2, and acetyl chloride/BTEA-NO2 was equally effective (~ 85%, without chromatography). TMS-Br/tert-butyl nitrite/dibromomethane gave crystalline 2- bromo-6-chloro analogue 3 (85%).(Chloro or bromo)-dediazoniation of 3', 5'-di-O-acetyl-2' ...