Starting from 2, 4-dichloroquinazoline, various methods for the selective removal of the 4- chloro substituent were tested, including catalytic hydrogenation, metal–halogen exchange, metal hydride reduction and reduction with tributyltin hydride—the latter both in a radical and in a Stille-type reaction. Amongst these, the most efficient method was found to be the Stille- type coupling. Furthermore, we have studied the reactivity of 2-chloroquinazoline and ...