Diisopropylethylamine → N,N'-bis(tert-butoxycarbonyl)-N''-(2-methyl-5-(4-methylpyridin-2-yl)phenyl)guanidine

Participants

Reaction Steps

To a suspension of 2-methyl-5-(4-methylpyridin-2-yl)aniline (285 mg), N,N′-bis(tert-butoxycarbonyl)thiourea (475 mg) and diisopropylethylamine (0.577 ml) in dichloromethane (15 ml) was added 1-methyl-2-chloropyridinium iodide (478 mg), and the mixture was stirred for 2 hours. The mixture was diluted with dichloromethane, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. To the residue was added 2-propanol, and the mixture was stirred. The precipitate was collected by filtration and dried to give N,N′-bis(tert-butoxycarbonyl)-N″-(2-methyl-5-(4-methylpyridin-2-yl)phenyl)guanidine (527 mg).

Provenance & Evidence