Abstract Oxidative cyclization of 6-chloro-4-pyrimidinylhydrazones 4 with iodobenzene diacetate (IBD) in dichloromethane gives rise to [1, 2, 4] triazolo [4, 3-c] pyrimidine derivatives 5a–o. These incipient products undergo feasible Dimroth rearrangement to furnish the isolated [1, 2, 4] triazolo [1, 5-c] pyrimidines 6a–o in moderate to high yields.