Synthetic applications of polymer-bound purine and pyrimidine bases

Abstract

Synthetic applications of polymer-bound purine and pyrimidine derivatives, based on their tautomerism, have been studied. The chloropyrimidine derivatives, which were highly reactive and could revert to the more stable lactam form, were particularly useful for dehydration and dehydrosulfanylation reactions. Alkoxypyrimidines were thermally cleaved to give olefins or esters, causing lactim to lactam transformation. Dissociation of alkylthio groups from thioalkylpurines and thioalkylpyrimidines took place under basic conditions to give olefins, indicating another example of tautomeric transformation.