Sodium hydride → 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-[1,2,4]triazolo[4,3-b]pyridazine

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To a solution of (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (100 mg, 0.53 mmol) in DMF (2 mL) was added sodium hydride (55% dispersion in mineral oil, 25.4 mg, 0.58 mmol). The mixture was stirred at room temperature for 15 min. After addition of 6-chloro-1,2,4-triazolo[4,3-b]pyridazine (90 mg, 0.58 mmol) the mixture was stirred at room temperature for another 2 h. Then the mixture was evaporated, extracted (ethyl acetate/water) and the organic phase was dried with sodium sulfate and concentrated. Chromatography (SiO2, dichloromethane:methanol=100:0 to 9:1) afforded the title compound (80 mg, 51%) as a white solid. MS: m/e=308.4 [M+H]+.

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