Water → 7-(4-chlorophenyl)-5-methyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

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Reaction Conditions

Reaction Steps

To a stirred solution of 7-chloro-5-methyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (2.0 g, 5.8 mmol), 4-chlorophenylboronic acid (1.2 g, 7.58 mmol), and tetrakis(triphenylphosphine)palladium (0.67 g, 0.58 mmol) in toluene (25 mL) at room temperature under argon was added aqueous Na2CO3 solution (2 M, 5.8 mL, 11.6 mmol). The resulting reaction mixture was stirred at 100° C. under argon overnight, after which time analysis by HPLC/MS indicated that the reaction was complete. After cooling the reaction mixture to room temperature, water (50 mL) was added. The resulting mixture was extracted with EtOAc (50 mL). The organic layer was washed with saturated aqueous NaCl, then dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by triturating with MeOH (15 mL) to obtain 1.95 g of the title compound as an off-white solid. HPLC/MS: retention time=3.85 min, [M+H]30 =420.

Provenance & Evidence