Heterocyclic studies. Part XVI. Imidazo- and di-imidazo-pyrimidines

Abstract

Condensation of 2,4-dichloro-6-methyl-5-nitropyrimidine with 2-chloroethylamine gave a tetrahydrodi-imidazopyrimidine (VII). Treatment of the 2,4-bis-(2′-hydroxyethyl)aminopyrimidine (VI; X = Y = NH·CH₂·CH₂·CH) with phosphoryl chloride gave a hydrated derivative (VIII) of the same di-imidazopyrimidine. The hydrated compound (VIII) was also prepared from a dihydroimidazo[1,2-c]pyrimidine (III; X = NH·CH₂·CH₂·OH), from a dihydroimidazo[1,2-a]pyrimidine (IX), and from (VII). 4,6-Dichloro-2-methyl-5-nitropyrimidine and 2-chloroethylamine gave a bis-2-chloroethylaminopyrimidine (XXI; X = NH·CH₂·CH₂Cl) which cyclised in two steps to give a dihydroimidazo[1,2-c]pyrimidine (XXII) and then the quaternary tricyclic compound (XXIII). ¹H n.m.r. and mass spectra of some compounds are presented.