A stepwise synthetic approach involving substitution of 6-chloro-1,3-dialkyluracils (5 and 6) with 3-(tert-amino)-2-hydroxypropylamines and subsequent acylation at C5 of uracil has been used to synthesize pyrimidinediones 27–33 in 61–89% overall yield. The conformational aspects of the new molecules based upon NMR data have been discussed.