Potassium Carbonate → 3-Isobutyl-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-quinazolin-4-one

Participants

Reaction Conditions

Reaction Steps

In a flask containing of 2-{1-[4-(4-Methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-quinazolin-4-one (50.0 mg, 0.12 mmol) in DMF was added I-Iodo-2-methylpropane (42.0 mg, 0.24 mmol), K2CO3 (80.0 mg, 0.6 mmol). The mixture was heated at 90° C. for 2 hours with stirring. After cooling down to room temperature, the excess K2CO3 was filtrated; the solution was treated with TFA (0.5 ml) and water (0.1 ml) with stirring at 90° C. for 2 hrs. Purification by HPLC (Gilson-215, 0.035% TFA in acetonitrile and 0.05% water as mobile phase) yielded 3-Isobutyl-2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-3H-quinazolin-4-one (Yield 21.0 mg, 37.0%) that was dried under reduced pressure. 1H NMR (400 MHz, DMSO-6): δ 0.98 (d, 3H, J=6.82 Hz), 1.01 (d, 3H, J=6.82 Hz), 1.76 (d, 3H, J=6.82 Hz), 2.08-1.99 (m, 1H), 3.51-3.19 (m, 6H), 3.86-3.75 (m, 2H), 3.93 (s. 3H), 4.16-3.93 (m, 2H), 4.84 (q, 1H, J=12.88, 7.07 Hz), 7.03 (dd, 2H, J=6.82, 2.27 Hz), 7.57 (dt, 1H, J=8.08, 1.01 Hz), 7.67 (dd, 2H, J=6.82, 2.27 Hz), 7.71 (d, 1H, J=8.08, Hz), 7.82 (dt, 1H, 8.59, 1.52 Hz), 8.39 (dd, 1H, J=8.08, 1.52 Hz). MS m/z calc. 484.21, found (ESI); 485.3 (M+1)+. Retention time 2.83 minutes.

Provenance & Evidence