MECHANISM OF FORMATION OF N-2-BENZYLGUANINE IN THE REACTION OF 2-AMINO-6-CHLOROPURINE WITH SODIUM BENZYL OXIDE, AND BENZYLATION OF NUCLEIC-ACID BASES

The mechanism of formation of N-2-benzylguanine in the reaction of 2-a mino-6-chloropurine with a large excess (12-13 molar eq) of sodium ben zyl oxide in benzyl alcohol at 130 degrees C was studied. N-2,O-6-Dibe nzylguanine, a reaction intermediate, was isolated and a possible mech anism for its formation is discussed, Furthermore, using this sodium b enzyl oxide system, benzylation at the amino group of nucleic acid bas es was facilitated.