Potassium Carbonate → 5-(1-(7-Chloroquinazolin-2-YL)piperidin-4-YL)-7,7-dimethyl-5H-pyrrolo[2,3-B]pyrazin-6(7H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 7,7-dimethyl-5-(piperidin-4-yl)-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one hydrochloride (Intermediate 78) (0.150 g, 0.530 mmol, Intermediate 57), 2,7-dichloroquinazoline (0.127 g, 0.637 mmol), and potassium carbonate (0.257 g, 1.857 mmol) in DMSO (3 mL) was heated at 110° C. in 2 h. The reaction mixture was cooled, H2O was added, and the solid was collected, purified by ISCO (30% EtOAc/Hexanes) to give the title compound (165 mg, 76%). MS (M+1): 409. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.25 (1 H, s), 8.08 (1 H, d, J=3.1 Hz), 8.12 (1 H, d, J=3.1 Hz), 7.89 (1 H, d, J=8.6 Hz), 7.54 (1 H, d, J=1.8 Hz), 7.29 (1 H, dd, J=8.6, 2.0 Hz), 5.02 (2 H, d, J=13.3 Hz), 4.60 (1 H, tt, J=12.2, 4.0 Hz), 2.92-3.15 (2 H, m), 2.42 (2 H, qd, J=12.6, 4.4 Hz), 1.82 (2 H, d, J=9.8 Hz), 1.32 (6 H, s).

Provenance & Evidence