Water → 7-(4-chlorophenyl)-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 suspension of 7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (738 mg, 3.0 mmol) in DMF (5 mL) at room temperature under argon was added 5-(chloromethyl)-2-(trifluoromethyl)pyridine (647 mg, 3.3 mmol), followed by K2CO3 (828 mg, 6.0 mmol). The resulting mixture was heated at 60° C. for 48 h, 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 (2×25 mL). The combined organic layers were washed with saturated aqueous NaCl, then dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting residue was triturated with chloroform (3×20 mL) and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography eluted with ethyl acetate-dichloromethane to obtain 206 mg of the title compound as a solid. HPLC/MS (methanol-water with 10 mM NH4OAc): retention time=3.58 min, [M+H]30 =406.

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