Development of a practical synthesis of a purine nucleoside phosphorylase inhibitor: BCX-4208

VP Kamath, JJ Juarez-Brambila…

Index: Kamath, Vivekanand P.; Juarez-Brambila, Jesus J.; Morris, Christopher B.; Winslow, Christopher D.; Morris Jr., Philip E. Organic Process Research and Development, 2009 , vol. 13, # 5 p. 928 - 932

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Citation Number: 24

Abstract

A practical synthesis of the purine nucleoside phosphorylase (PNP) inhibitor BCX-4208 (1) was accomplished in three telescoped steps. Mannich condensation of the 4-benzyloxy-9- deazahypoxanthine with (3 R, 4 R)-3-hydroxy-4-(hydroxymethyl) pyrrolidine and formaldehyde followed by removal of the protecting group and crystallization furnished the desired product as a hydrochloride salt in 85% overall yield and 99.8% purity. A scalable ...