Water → 5-(4,4-Dimethyl-2-oxo-1,4-dihydro-2H-benzo[d][1,3]oxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile

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Reaction Steps

To a solution of 5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1H-pyrrole-2-carbonitrile (1 eq, 71 mg, 0.27 mmol) in dimethylformamide (0.5 mL) was added potassium carbonate (5 eq, 0.18 g, 0.1.35 mmol). After 10 min., iodomethane (3 eq, 0.05 mL, 0.81 mmol) was added and the suspension was stirred for 2 h, poured into water (5 mL) and extracted with ethyl acetate (3×5 mL). The layers were separated, the aqueous layer was extracted with ethyl acetate (3×10 mL) and the combined organic layer was washed with brine, dried over MgSO4 and purified by flash column chromatography on silica gel eluting with 30% ethyl acetate/hexane to give 5-(4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile (30 mg, 41%) as a white solid. 1H NMR (300 MHz, d6-DMSO) δ 1.64 (s, 6 H), 3.71 (s, 3 H), 6.33 (d, 1 H, J=4.1 Hz), 6.98 (d, 1H, J=8.0 Hz), 7.03 (d, 1H, J=4.1 Hz), 7.39 (m, 2 H), 10.39 (s, 1 H). MS (APCI (−)) m/z 280 (M−H)−. Anal. calcd for C16H15N3O2, C, 68.3, H, 5.37, N, 14.9. Found, C, 68.4, H, 5.51, N, 14.6.

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