Cesium carbonate → N2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-N4-methyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-2,4-diamine

Participants

Reaction Conditions

Reaction Steps

2-Chloro-N-methyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-amine (161 mg, 0.63 mmol), 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (256 mg, 1.26 mmol), cesium carbonate (410 mg, 1.26 mmol), palladium(II) acetate (21 mg, 0.09 mmol) and 2-(dicyclohexylphosphino)biphenyl (33 mg, 0.09 mmol) were mixed in dioxane (10 mL) under an atmosphere of nitrogen. The vial was heated in microwave reactor at 120° C. for 90 min. The mixture was filtered through a plug of diatomeous earth which was eluted with MeOH. The mixture was partitioned between EtOAc and sodium hydroxide (1 M, aq). The organic layer was dried over sodium sulfate and concentrated in vacuum. The residue was purified by preparative HPLC to give the title compound as a solid 136 mg (51%).

Provenance & Evidence