Methanol → 1-cyclobutyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

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Reaction Steps

Under an argon atmosphere, to a solution of 5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4-ol (2.0 g) in DMF (40 mL) was added under ice-cooling 60% sodium hydride (596 mg), and the mixture was stirred for 1.5 hr. Then, bromocyclobutane (1.05 mL) was added, and the mixture was stirred at room temperature for 16 hr. To the reaction mixture was added methanol, and the mixture was concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate/methanol) and further purified by HPLC to give the title compound (0.92 g).

Provenance & Evidence