Tetrahedron Letters

An unexpected cyclization discovered during the synthesis of 8-substituted purines from a 4, 5-diaminopyrimidine

Q Dang, RM Rydzewski, DK Cashion, MD Erion

Index: Dang, Qun; Rydzewski, Robert M.; Cashion, Daniel K.; Erion, Mark D. Tetrahedron Letters, 2008 , vol. 49, # 13 p. 2143 - 2145

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Citation Number: 2

Abstract

Attempted conversion of 4-chloro-5-(N-4-bromobutanoyl) amino-6- phenethylaminopyrimidine (2) to 6-chloro-8-[1-(3-bromo) propyl]-9-phenethylpurine (1) under standard cyclization conditions did not give the targeted product. Instead, an unexpected cyclization occurred to give 6-chloro-5-[1-(3-hydroxy) propyl]-9-phenethylpurine (3), which can be viewed as a hydrolysis product of the resulting halide. The cyclization ...