Alkylation of 6-N-acylated adenosine derivatives by the use of phase transfer catalysis

Abstract

6-N- or N¹-Alkylation of 6-N-acyl adenosine derivatives with alkyl halides in CH₂Cl₂–1 mol dm^–3 NaOH in the presence of Bu₄NBr has been studied. A variety of N-acyl groups have been examined. Consequently, the use of the acetyl and 2-(trimethylsilyl)ethoxycarbonyl groups resulted in the corresponding 6-N-alkylated products in high yields. It was also found that, when the benzoyl group was chosen as the N-acyl group, N¹-alkylated products were obtained along with 6-N-alkylated products. The structure of the 6-N- and N¹-alkylated adenosine derivatives has been determined by¹H And¹³C NMR spectroscopy.