Potassium Carbonate → HCID 89783636, compound

Participants

Reaction Conditions

Reaction Steps

Argon was bubbled into a slurry of potassium carbonate (Mallinkrodt; 0.074 g, 0.536 mmol), dichlorobis(p-dimethylaminophenylditbutylphosphine)palladium(ii) (Aldrich; 4.74 mg, 6.70 μmol), (R)-6-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (705; 0.070 g, 0.268 mmol), 8-bromo-2-(tert-butylamino)-3-(pyridin-3-yl)quinazolin-4(3H)-one (404a; 0.050 g, 0.134 mmol) for 1 min. The reaction was sealed and heated to 80° C. for 30 min. The reaction was adsorbed onto 0.7 g silica gel and dried in vacuo. The material was treated with purified by silica gel chromatography (12 g column) using 0-100% (90/10 DCM/MeOH) in DCM. The product-containing fractions were concentrated to afford (R)-2-(tert-butylamino)-8-(6-methyl-4-oxo-1,4,5,6-tetrahydropyrrolo[3,4-b]pyrrol-2-yl)-3-(pyridin-3-yl)quinazolin-4(3H)-one (0.042 g, 0.098 mmol, 73% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.91 (1H, s), 8.74 (1H, dd, J=4.9, 1.6 Hz), 8.64 (1H, d, J=2.2 Hz), 7.91-7.99 (2H, m), 7.89 (1H, dd, J=7.8, 1.6 Hz), 7.59-7.69 (2H, m), 7.24 (1H, t, J=7.6 Hz), 6.77 (1H, d, J=1.6 Hz), 4.61 (1H, s), 4.49-4.58 (1H, m), 1.31-1.41 (12H, m). m/z (ESI, +ve ion) 429.0 (M+H)+.

Provenance & Evidence