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

Participants

Reaction Steps

To a suspension of 2-chloro-5-(4-methoxypyridin-2-yl)aniline (165 mg), N,N′-bis(tert-butoxycarbonyl)thiourea (233 mg) and diisopropylethylamine (0.28 ml) in dichloromethane (7 ml) was added 1-methyl-2-chloropyridinium iodide (232 mg), and the mixture was stirred for 16 hours. The mixture was diluted with dichloromethane, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 30 g, n-hexane:ethyl acetate=2:1) to give N,N′-bis(tert-butoxycarbonyl)-N″-(2-chloro-5-(4-methoxypyridin-2-yl)phenyl)guanidine (144 mg).

Provenance & Evidence