Combinatorial synthesis of heterocycles: Solid-phase synthesis of 6-amino-2,4-dioxo-3,4-dihydro-1,3,5-triazine derivatives

A new solid-phase synthesis of trisubstituted 6-amino-2,4-dioxo-3,4-dihydro -1,3,5-triazines From a resin-bound amine component is described. The amine was readily converted to the corresponding palymerbound S-methylthiopseudo urea, which upon reaction with secondary amines gave the disubstituted guan idines. Cyclization of the polymer-bound guanidines with chlorocarbonylisoc yanate afforded the triazinediones. The third point of diversity was introd uced by the Mitsunobu reaction. The method is amenable for iterative combin atorial library generation.