Sodium Carbonate → 1-((8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methyl)-3-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Participants

Reaction Steps

Prepared according to Procedure J using 3-iodo-1-((8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.1000 g, 0.178 mmol, 1 eq), pyrazole-4-boronic acid pinacol ester (0.0693 g, 0.357 mmol, 2.0 eq), tetrakis(triphenylphosphine)palladium(0) (0.0206 g, 0.0178 mmol, 10 mol %), and sodium carbonate (2M aq. sol, 0.535 mL, 1.07 mmol, 6 eq) in DMF (1 mL). After purification, 1-((8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methyl)-3-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine was obtained as white solid. The white solid was suspended in CH2Cl2 and filtered to give the desired product as white solid [PI3Kδ IC50=8 nM]. 1H NMR (DMSO-d6) δ ppm 13.17 (1 H, s), 8.22 (1 H, s), 7.97-8.08 (2 H, m), 7.71-7.90 (3 H, m), 7.56-7.66 (3 H, m), 7.52 (1 H, dd, J=7.8, 7.0 Hz), 7.35-7.44 (1H, m), 6.82 (2 H, br. s.), 5.42-5.55 (2 H, m), 2.60 (3 H, s). Mass Spectrum (ESI) m/e=501.1 (M+1).

Provenance & Evidence