Sodium Carbonate → 3-(4-Amino-1-((8-methyl-2-o-tolylquinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)phenol

Participants

Reaction Conditions

Reaction Steps

Prepared according to Procedure J. A mixture of 3-iodo-1-((8-methyl-2-o-tolylquinolin-3-yl)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (51 mg, 0.1 mmol), 3-hydroxyphenylboronic acid (15.2 mg, 1.1 eq), sodium carbonate (55 mg, 5 eq), tetrakis(triphenylphosphine)palladium (6 mg, 5% mmol) in DMF (1 mL) and water (0.3 mL) was heated to 100° C. under N2 for 4 h. The reaction mixture was cooled to room temperature, filtered and purified by reverse HPLC (MeCN/H2O/0.1% TFA) on C18 to give a white solid [PI3Kδ IC50=7 nM]. 1H-NMR (DMSO-d6) δ 8.37 (s, 1H), 8.35 (s, 1H), 7.86 (d, J=8.2 Hz, 1H), 7.65 (d, J=7.0 Hz, 1H), 7.53 (t, J=7.4 Hz, 1H), 7.31 (t, J=7.8 Hz, 1H), 7.14-7.17 (m, 4H), 6.87-6.97 (m, 4H), 5.63 (s, br, 2H), 2.63 (s, 3H), 1.91 (s, 3H). Mass Spectrum (ESI) m/e=473 (M+1).

Provenance & Evidence