Sodium methanesulfinate → 2-Ethyl-6-methanesulfonyl-3-methyl-3H-quinazolin-4-one

Participants

Reaction Steps

The substrate of 6-bromo-2-ethyl-3-methyl-3H-quinazolin-4-one (50.0 mg, 0.189 mmol), sodium methanesulfinate (28.8 mg, 0.29 mmol) and copper (I) iodide (53.7 mg, 0.29 mmol) was placed in a flask, which was flushed with N2. DMF (2 ml) was added via syringe. The resulting mixture was irradiated at 180° C. for 30 minutes in the SmithSynthesizer Microwave reactor (Personal Chemistry) with vigorous agitation by a magnetic stirrer. The mixture was cooled to room temperature, diluted with ethyl acetate (5 ml), and then filtered. The filtrate was washed with water and brine, dried over anhydrous MgSO4, and concentrated by rotary evaporation. Purification was accomplished by HPLC (Gilson-215, 0.035% TFA in acetonitrile and 0.05% water as mobile phase). The product was collected and dried under reduced pressure to give 2-Ethyl-6-methanesulfonyl-3-methyl-3H-quinazolin-4-one (Yield 12.5 mg, 25.1%). 1H NMR (400 MHz, CDCl3): δ 1.35 (t, 3H, J=7.58 Hz), 2.83 (dd, 2H, J=14.65, 7.58 Hz), 3.02 (s, 3H), 3.58 (s, 3H), 7.73 (d, 1H, J=8.84 Hz), 8.12 (dd, 1H, J=8.84 Hz), 8.77 (d, 1H, J=2.02 Hz). MS m/z calc. 265.1, found (ESI); 266.0 (M+1)+. Retention time 2.41 minutes.

Provenance & Evidence