A new approach to the synthesis of NN-dialkyladenine derivatives

Abstract

N,N-Dialkyladenine derivatives were prepared by two different reaction sequences starting from 5-amino-4-cyanoformimidoylimidazoles. When these imidazoles were treated with dimethylformamide diethyl acetal, a 5-aminomethyleneamino-4-cyanoformimidoylimidazole was isolated and evolved to the N,N-dialkyladenine in the presence of a secondary alkylamine. The same purine structure was isolated when the 5-amino-4-cyanoformimidoylimidazole was first treated with a secondary amine to give a stable 4-amidino5-aminoimidazole. The desired product was generated when the 4-amidino-5-aminoimidazole was combined with dimethylformaraide diethyl acetal, at room temperature.