Dichloromethane → 2-((4-amino-3-(3-aminophenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)methyl)-3-phenyl-4H-chromen-4-one

Participants

Reaction Conditions

Reaction Steps

To a solution of Example 57a (0.400 g, 0.804 mmoles) in DMF (10 ml), ethanol (5 ml) and water (5 ml), 3-Acetamidophenyl boronic acid (0.187 g, 1.045 mmoles) and sodium carbonate (0.426 g, 4.02 mmoles) were added and the system is degassed for 30 min. Palladium tetrakis triphenylphosphine (0.183 g, 0.158 mmoles) was added under nitrogen atmosphere and heated to 80° C. After 12 h, the reaction mixture was celite filtered, concentrated and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. To the concentrate ethanol (5 ml) and Con.HCl (0.5 ml) were added and refluxed for 2 h. The reaction mixture was basified with sodium carbonate solution and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with methanol: dichloromethane to afford the title compound as yellow solid (0.140 g, 38% yield). MP: 157-159° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 8.21(s,1H), 8.06(dd, J=7.8,1.3 Hz, 1H),7.77(dt, J=8.6,1.5 Hz, 1H),7.49(t, J=7.4 Hz, 1H),7.37-7.29(m,5H), 7.17(t, J=7.7 Hz, 1H), 6.84(s,1H), 6.71(d, J=7.5 Hz, 1H),6.65(d, J=7.9 Hz, 1H), 5.51(s,2H), 5.34(s, 2H). Mass: 460.84(M+).

Provenance & Evidence