Cesium carbonate → 6-[4-(4-Amino-pyridin-2-yl)-phenyl]-5-(4-chloro-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Participants

Reaction Conditions

Reaction Steps

A reaction tube charged with 5-(4-chloro-phenyl)-1-phenyl-6-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (20.0 mg, 0.038 mmol), 4-amino-2-chloropyridine (9.8 mg, 0.076 mmol), Cs2CO3 (24.8 mg, 0.076 mmol), Pd2(dba)3 (1.7 mg, 0.002 mmol), and 1,3-bis-(2,6-diisopropyl-phenyl)-3H-imidazol-1-ium chloride (1.6 mg, 0.004 mmol) is purged with nitrogen. Anhydrous 1,4-dioxane (0.5 mL) is added via syringe. The reaction mixture is heated at 120° C. for 3 days, cooled down to room temperature, taken in H2O (5 mL), and extracted by ethyl acetate (3×3 mL). The combined organic phase is concentrated and purified by reverse phase HPLC to provide the title compound; 1H NMR (CDCl3, 400 MHz) δ 8.34 (s, 1H), 8.09 (d, 2H), 8.06 (d, 1H), 7.63 (d, 2H), 7.54 (t, 2H), 7.44 (d, 2H), 7.39 (t, 1H), 7.29 (d, 2H), 7.03 (d, 2H), 6.89 (s, 1H), 6.59 (d, 1H); HPLC-MS calculated for C28H19ClN6O (M+H+) 491.1. Found: 491.1.

Provenance & Evidence