Sodium hydride → 6-((1S,4S)-5-Methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-3-((5-methylisoxazol-3-yl)methyl)quinazolin-4(3H)-one

Participants

Reaction Steps

To a solution of 6-((1S,4S)-5-Methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)quinazolin-4(3H)-one (Example 10A) (150 mg, 0.583 mmol) in dimethylformamide was cooled to 0° C. added and sodium hydride (21 mg, 0.875 mmol) was added, after 5 minutes 3-bromomethyl-5-methylisoxazole (75 mg, 0.426 mmol) was added and the reaction stirred at room temp for 1 h. The reaction was quenched with ammonium chloride and the dimethylformamide evaporated off. The residue was dissolved in 10% methanol in dichloromethane and dried over sodium sulphate before evaporation to dryness. The product was purified by silica chromatography, elueting with 10% methanol in dichloromethane to afford 6-((1S,4S)-5-Methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-3-((5-methylisoxazol-3-yl)methyl)quinazolin-4(3H)-one (0.10 g, 0.284 mmol).

Provenance & Evidence