A number of N-substituted azacalix [4] pyrimidines were synthesized by two methods. While straightforward condensation reaction between 4, 6-dichloropyrimidine and 4, 6-bis (alkylamino) pyrimidines gave identically N-substituted azacalix [4] pyrimidines in low yields, a general and moderate-to-high yielding 1+ 3 macrocyclic fragment coupling reaction afforded azacalix [4] pyrimidines that contained either the same or different N-substituents. ...