The synthesis of bisguanidinoalkanes and guanidinoalkanes, N- or N′-substituted with pyrimidines, as analogues of chlorhexidine

A series of N,N‴-alkanediylbis[N′-(5-halopyrimidin-2-yl)guanidine] salts has been synthesized along with N,N‴-(trans-cyclohexane-1,4-diyl)bis[N′-(5-chloropyrimidin-2-yl) guanidine], N,N‴-(ciscyclohexane-1,4-diyl)bis[N′-(5-chloropyrimidin-2-yl) guanidine] dihydrochloride and N-(cis-4-aminocyclohexan-1-yl)-N′-(5-chloropyrimidin-2-yl)guanidine dihydrochloride. Furthermore, a series of N-(alkan-1-yl)-N′-(5-chloropyrimidin-2yl)guanidine hydrochlorides and N-(6-aminohexan-1-yl)-N′-(5-chloropyrimidin-2-yl)guanidine dihydrochloride were synthesized. This series of compounds was prepared by displacement reactions of 2-methylsulfonylpyrimidines with bisguanidinoalkanes or by condensation of 5-chloro-2-cyanoaminopyrimidine (5-chloropyrimidin-2-ylcyanamide) with alkylamines.