Diisopropylethylamine → N,N'-bis(tert-butoxycarbonyl)-N''-(3-(4-methoxypyridin-2-yl)phenyl)guanidine

Participants

Reaction Steps

To a suspension of 3-(4-methoxypyridin-2-yl)aniline (130 mg), N,N′-bis(tert-butoxycarbonyl)thiourea (216 mg) and diisopropylethyl-amine (0.26 ml) in dichloromethane (6.5 ml) was added 1-methyl-2-chloropyridinium iodide (216 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. The residue was purified by column chromatography (silica gel 25 g, n-hexane:ethyl acetate=4:1) to give N,N′-bis (tert-butoxycarbonyl) -N″- (3- (4-methoxypyridin-2-yl) phenyl) guanidine (240 mg).

Provenance & Evidence