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Paper | Regular issue | Vol 36, No. 8, 1993, pp.1883-1895
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6395
Protection and Deprotection of Fused 2-Amino-4(3H)-pyrimidinones: Conversion of Pterins and 5-Deazapterins to 2,4-Diamino Derivatives

Edward C. Taylor,* S. R. Otiv, and (in part) Inci Durucasu

*Department of Chemistry, Princeton University, Princeton, New Jersey 08544, U.S.A.

Abstract

5-Deazapterins and pterins are readily converted to their 4-deoxy-4-amino derivatives (a lactam-to-amidine conversion) by reaction with 4-chlorophenyl phosphorodichloridate and 1,2,4-triazole to give intermediate 4-[1’-(1,2,4-triazolyl)] derivatives, followed by reaction with aqueous ammonia. Some anomalous results obtained by application of the Mitsunobu reaction (normally a lactam-to-lactim ether conversion) to 5-deazapterins are detailed.