Synthesis of isomeric N-(3-fluoro-2-hydroxypropyl) and N-(2-fluoro-3-hydroxypropyl) derivatives of purine and pyrimidine bases

J Jindřich, H Dvořáková, A Holý

Index: Jindrich, Jindrich; Dvorakova, Hana; Holy, Antonin Collection of Czechoslovak Chemical Communications, 1992 , vol. 57, # 7 p. 1466 - 1482

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Citation Number: 4

Abstract

Abstract Reaction of fluoromethyloxirane (III) with heterocyclic bases in the presence of potassium carbonate afforded N-(3-fluoro-2-hydroxypropyl) derivatives of adenine (VI), 3- deazaadenine (VII), 2-amino-6-chloropurine (XII), 6-nitro-1-deazapurine (IX), 4-methoxy-2- pyrimidone (XVIII) and its 5-methyl derivative (XIX). Acid hydrolysis of compounds XII, XVIII, and XIX gave 9-(3-fluoro-2-hydroxypropyl) guanine (XIII), 1-(3-fluoro-2-hydroxypropyl) ...