5-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one → 7,8-bis(4-chlorophenyl)-5-methyl-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

Participants

Reaction Steps

To a stirred solution of 5-chloro-7,8-bis(4-chlorophenyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (50 mg, 0.128 mmol) and tetrakis(triphenylphosphine)palladium (7 mg, 0.006 mmol) in THF (0.5 mL) at room temperature under argon was added 2.0 M methylzinc chloride solution in THF (0.25 mL, 0.5 mmol). The reaction mixture was stirred at reflux for 1.5 h. The reaction mixture was cooled in an ice bath and quenched with saturated aqueous NH4Cl. EtOAc (5 mL) and water (5 mL) were added and the layers were separated. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluted with 40% EtOAc-hexanes to obtain 40 mg of the title compound as a white solid. HPLC/MS: retention time=3.883 min, [M+H]30 =371.

Provenance & Evidence