Water → 6-{5-amino-3-phenyl-6-[(trimethylsilyl)ethynyl]-2-pyrazinyl}-2-isopropyl-3(2H)-pyridazinone

Participants

Reaction Conditions

Reaction Steps

In the presence of copper(I) iodide (25 mg) and dichlorobis(triphenylphosphine)palladium(II) (91 mg), triethylamine (0.397 ml) was dropwise added to a mixture of 6-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (1.00 g) and ethynyl(trimethyl)silane (0.716 ml) in 1,2-dichloroethane (20 ml) under ice-cooling. The mixture was stirred at same temperature for one hour and at 25-30° C. for 18 hours. After addition of water, an organic layer was collected, washed with sat. aq. sodium chloride, dried over MgSO4 and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (80:20 v/v) to give a solid. The solid was crystallized from a mixture of acetone and n-hexane to give 6-{5-amino-3-phenyl-6-[(trimethylsilyl)ethynyl]-2-pyrazinyl}-2-isopropyl-3(2H)-pyridazinone (431 mg).

Provenance & Evidence