1,4-Diazabicyclo[2.2.2]octane (DABCO)-catalysed hydrolysis and alcoholysis reactions of 2-amino-9-benzyl-6-chloro-9H-purine

Abstract

2-Amino-9-benzyl-6-chloro-9H-purine 1 is hydrolysed in refluxing water in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) to give 2-amino-9-benzyl-1,6-dihydro-6-oxo-9H-purine 3; however, 1 reacts with hydroxide ion at ambient temp., or analcohol and potassium carbonate at elevated temperatures, in the presence of DABCO togive 3 or 6-alkoxy-2-amino-9-benzyl-9H-purines 4–8, respectively.