Purines. LVIII. A Synthesis of 7-Alkyl-1-methyladenines from Adenosine by Regioselective Alkylation : Uilization of a 1-Methoxy Group as a Control Synthon

Abstract

A general synthetic route to 7-alkyl-1-methyladenine (8) from N⁶-methoxy-1-methyladenosine (5) in three steps [hence from adenosine (1) in seven steps] has been established. The route started with alkylation of 5, readily obtainable from 1 in four steps according to previously reported procedures, and proceeded through glycosidic methanolysis of the resulting 7-alkylated nucleoside (6) and removal of the N⁶-methoxy group by catalytic hydrogenolysis.