2-Bromobenzonitrile → 2-[(3R)-3-methyl-4-(1-methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yl)-piperazin-1-yl]-benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-methyl-2-((2R)-2-methyl-piperazin-1-yl)-1H-[4,4′]bipyrimidinyl-6-one (150 mg, 0.524 mmol) in ethylene glycol dimethyl ether (2.0 ml) was added 2-bromobenzonitrile (143 mg, 0.786 mmol), tris(dibenzylideneacetone)dipalladium (24 mg, 0.026 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (25 mg, 0.052 mmol) and tripotassium phosphate (167 mg, 0.786 mmol), and the reaction mixture was stirred for 12 hours at 80° C. The reaction was quenched with water, the aqueous layer was extracted with ether. The extract was washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was purified with HPLC to afford 2-[(3R)-3-methyl-4-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yl)-piperazin-1-yl]-benzonitrile (120 mg, 0.310 mmol, 59%) as pale yellow crystals.

Provenance & Evidence