4-(4-Bromobenzyl)piperazine, N1-BOC protected → Tert-butyl 4-{4-[4-(1-methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yloxy)piperidin-1-yl]benzyl}piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of tert-butyl 4-(4-bromo-benzyl)piperazine-1-carboxylate (371 mg, 1.04 mmol), 1-methyl-2-(piperidin-4-yloxy)-1H-[4,4′]bipyrimidinyl-6-one (300 mg, 1.04 mmol), tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (43.2 mg, 41.8 μmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (79.6 mg, 0.167 mmol) in toluene (2.09 ml) was added sodium tert-butoxide (151 mg, 1.57 mmol) under nitrogen atmosphere. The mixture was stirred at 150° C. for 30 minutes in Biotage Microwave reactor. The mixture was filtered through a pad of Celite, and concentrated in vacuo. The residue was purified by NH-silica gel column chromatography (eluent; hexane/ethyl acetate=1/1) to afford tert-butyl 4-{4-[4-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yloxy)piperidin-1-yl]benzyl}piperazine-1-carboxylate as a pale yellow solid (236 mg, 0.420 mmol, 40%).

Provenance & Evidence