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

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-N-methyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-amine (85 mg, 0.33 mmol), 4-(4-methyl-1H-imidazol-1-yl)aniline (100 mg, 0.58 mmol), cesium carbonate (217 mg, 0.67 mmol), palladium(II) acetate (11 mg, 0.05 mmol) and 2-(dicyclohexylphosphino)-biphenyl (17 mg, 0.05 mmol) in dioxane (3 mL) was heated in a microwave reactor under notrogen atmosphere at 120° C. for 90 min. The reaction mixture was filtered through a pad of diatomeous earth which was eluted with MeOH. The mixture was partitioned between EtOAc and sodium hydroxide (aq, 1 M). The organic phase was separated, dried over sodium sulfate and concentrated in vacuum. The residue was purified by preparative HPLC to give the title compound as a solid 52 mg, (40%).

Provenance & Evidence