Methyl iodide → 7-bromo-1-methyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 7-bromo-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (500 mg, 2.183 mmol) in acetone (8 mL) at RT was added potassium carbonate (905 mg, 6.55 mmol) followed by methyl iodide (0.341 mL, 5.46 mmol). This was heated to 60° C. under nitrogen atmosphere for 3 hours. The reaction mixture was cooled to RT, solvent removed in vacuo. The residue was partitioned between water/ethyl acetate (ca. 25 mL each). The aqueous layer was extracted with ethyl acetate (ca. 25 mL twice). The combined organic layers were dried over MgSO4 and solvent removed in vacuo. The residue was purified on silica gel (eluted with 20-60% ethyl acetate/cyclohexane) to afford the title compound (334 mg). LCMS (A): m/z (M+H)+ 243/245, C8H7BrN2O2 requires 242/244 (acidic).

Provenance & Evidence