Diisopropylethylamine → HCID 135710956, compound

Participants

Reaction Steps

To a suspension of 3-(3-tert-butyldimethylsilyloxymethylpyridin-2-yl)aniline (364 mg), N,N′-bis(tert-butoxycarbonyl)thiourea (385 mg) and diisopropylethylamine (0.465 ml) in dichloromethane (12 ml) was added 1-methyl-2-chloropyridinium iodide (385 mg), and the mixture was stirred for 18 hours. The mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 35 g, 20% ethyl acetate in n-hexane) to give N,N′-bis(tert-butoxycarbonyl)-N″-(3-(3-tert-butyldimethylsilyloxymethylpyridin-2-yl)phenyl)guanidine (549 mg).

Provenance & Evidence