Regioselective solid-phase 4-amino-de-chlorination of 2,4,6-trichloropyrimidine by resin-supported N-potassium carbamates

The first regioselective resin-anchoring reaction of 2,4,6-trichloropyrimidine has been achieved through 4-amino-de-chlorination by solid-supported Boc-like N-potassium carbamates. Excellent regioselectivities together with high coupling efficiency were obtained with aliphatic, aromatic and α-amino-ester derived carbamates. The scope and limits of the reaction are described with the view of its applications to the solid-phase synthesis of combinatorial libraries of aminopyrimidine-based structures.