Cesium carbonate → racemic N-{3-[1-(cyclohex-2-en-1-yl)-1H-pyrazol-4-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

3-Bromocyclohexene (0.18 mL, 1.57 mmol) and cesium carbonate (1.02 g, 3.13 mmol) were added to an oven-dried flask containing N-[3-methyl-5-(1H-pyrazol-4-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (500 mg, 1.57 mmol) dissolved in DMF (5 mL). The mixture was warmed to 80° C. and stirred overnight. The mixture was cooled to room temperature, diluted with EtOAc, and washed with 1:1 water:brine (3×). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0 to 80% EtOAc/hexanes) to afford racemic N-{3-[1-(cyclohex-2-en-1-yl)-1H-pyrazol-4-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine. MS ESI calcd. for C21H21F3N5 [M+H]+ 400. found 400.

Provenance & Evidence