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

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 (0.1 g, 0.1785 mmol, 1 eq), 3-hydroxyphenylboronic acid (0.0492 g, 0.357 mmol, 2.0 eq), tetrakis(triphenylphosphine)palladium (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, 3-(4-amino-1-((8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol was obtained as light gray solid. The gray solid was suspended in CH2Cl2 and filtered to provide 3-(4-amino-1-((8-methyl-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol [PI3Kδ IC50=8 nM] as off-white solid. 1H NMR (DMSO-d6) δ ppm 9.65 (1 H, s), 8.28 (1 H, s), 8.04 (1 H, s), 7.87 (1 H, d, J=7.8 Hz), 7.74-7.80 (1 H, m), 7.64 (1 H, d, J=7.0 Hz), 7.56-7.61 (2 H, m), 7.50-7.56 (1 H, m), 7.34-7.38 (1 H, m), 7.30 (1 H, t, J=7.8 Hz), 6.94-7.02 (2 H, m), 6.80-6.87 (1 H, m), 5.53 (2 H, s), 2.60 (3 H, s). Mass Spectrum (ESI) m/e=527.2 (M+1).

Provenance & Evidence