4-Chloroaniline → [6-(5-Chloro-2-methoxy-phenyl)-2-methyl-pyrimidin-4-yl]-(4-chloro-phenyl)-amine

Participants

Reaction Conditions

Reaction Steps

To an argon saturated solution of 4-chloro-6-(5-chloro-2-methoxy-phenyl)-2-methyl-pyrimidine (50 mg, 0.18 mmol), 4-chloroaniline (23 mg, 0.18 mmol), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (66 mg, 0.1 mmol) and sodium tert-butoxide (26 mg, 0.27 mmol) in toluene (10 ml) was added tris(dibenzylideneacetone)-dipalladium (92 mg, 0.1 mmol). After stirring at 80° C. under an argon atmosphere for 6 hours, the mixture was concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:5 followed by 1:3) to provide the title compound (33 mg, 51% yield) as a white powder.

Provenance & Evidence