Purines. LVIII: A synthesis of 7-alkyl-1-methyladenines from adenosine by regioselective alkylation : utilization of a 1-methoxy group as a control synthon

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