Benzhydryl as an Efficient Selective Nitrogen Protecting Group for Uracils

Abstract

Regioselective N-substitution of the less active nitrogen within uracil analogues has been achieved following preliminary N-protection at the more active N-position with a benzhydryl protecting group. This protecting group is stable to concentrated HCl (aqueous) at reflux temperature, TFA at room temperature, and Pd-C-catalyzed normal pressure hydrogenation at room temperature; the benzhydryl group can be removed quantitatively and selectively with a 10% triflic acid solution in TFA at 0 degree C.