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

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Reaction Steps

To a solution of (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (60 mg, 0.32 mmol) in DMF (2 mL) was added sodium hydride (55% dispersion in mineral oil, 15 mg, 0.35 mmol). The mixture was stirred at room temperature overnight. After addition of a solution of 6-chloro-1,2,4-triazolo[4,3-b]pyridazine-3-carboxylic acid ethyl ester (79 mg, 0.35 mmol) in DMF (2 mL) the mixture was stirred at room temperature overnight. Then the mixture was evaporated, extracted (ethyl acetate/water) and the organic phase was dried with sodium sulfate and concentrated. Purification by preparative HPLC on reversed phase eluting with acetonitrile/water [0.1% aq NH3 (25%)] afforded the title compound (20 mg, 14%) as a white solid. MS: m/e=380.0 [M+H]+.

Provenance & Evidence