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-trichloropyrimid ine has been achieved through 4-amino-dechlorination by solid-supported Boc -like N-potassium carbamates. Excellent regioselectivities together with hi gh coupling efficiency were obtained with aliphatic, aromatic and alpha -am ino-ester derived carbamates. The scope and limits of the reaction are desc ribed with the view of its applications to the solid-phase synthesis of com binatorial libraries of aminopyrimidine-based structures. (C) 2001 Elsevier Science Ltd. All rights reserved.