Trimethylamine → HCID 136236446, compound

Participants

Reaction Conditions

Reaction Steps

To a cold solution of 2-(difluoro(methoxy)methyl)-1,1,1,3,3,3-hexafluoropropane (81 mg, 1 equiv.) in DMF (876 μl) at 0° C., was added, slowly, trimethylamine (98 μl, 2 equiv.). The mixture was stirred at 0° C. for 1 h. To this mixture, was added a solution of 1-(2-fluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazole-3-carboximidamide (Intermediate 8C, 100 mg, 1 equiv.) in DMF (876 μl). The mixture was stirred at room temperature for 1 h and heated to 70° C. for an additional 1 h. The mixture was cooled to room temperature. It was diluted in ethyl acetate (100 ml) and washed with water (50 ml×3). The organic layer was dried, filtered and evaporated to give solid. The resulting solid was dissolved in methanol and absorbed onto silica gel. Purification by column chromatography (0 to 100% ethyl acetate in hexanes) gave 6-fluoro-2-(1-(2-fluorobenzyl)-5-(isoxazol-3-yl)-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidin-4(3H)-one (35 mg, 24% yield) as a yellow solid.

Provenance & Evidence