Mechanism of Formation of N2-Benzylguanine in the Reaction of 2-Amino-6-chloropurine with Sodium Benzyl Oxide, and Benzylation of Nucleic Acid Bases

The mechanism of formation of N2-benzylguanine in the reaction of 2-amino-6-chloropurine with a large excess (12-13 molar eq) of sodium benzyl oxide in benzyl alcohol at 130°C was studied, N2, O6-Dibenzylguanine, a reaction intermediate, was isolated and a possible mechanism for its formation is discussed. Furthermore, using this sodium benzyl oxide system, benzylation at the amino group of nucleic acid bases was facilitated.