Cesium carbonate → HCID 57899386, compound

Participants

Reaction Conditions

Reaction Steps

A reaction tube charged with 5-(4-chloro-phenyl)-3-methanesulfonyl-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 (200.0 mg, 0.332 mmol), 2-amino-5-bromopyridine (114.8 mg, 0.664 mmol), Cs2CO3 (162.1 mg, 0.498 mmol), and Pd(dppf)2Cl2 (54.2 mg, 0.066 mmol) is purged with nitrogen. Anhydrous DMF (3.3 mL) is added via syringe. The reaction mixture is heated at 80° C. for 2 h, cooled down to room temperature, poured into water (30 mL) and EtOAc (30 mL). The insoluble solid is filtered off and the two layers of the filtrate are separated. The aqueous layer is extracted with EtOAc (2×30 mL). The combined organic phase is washed with brine, dried over MgSO4, concentrated, and purified by reverse phase HPLC to provide 6-[4-(6-amino-pyridin-3-yl)-phenyl]-5-(4-chloro-phenyl)-3-methanesulfonyl-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one as a light yellow solid product; 1H NMR (CDCl3, 400 MHz) δ 8.21 (d, 1H), 8.11 (d, 2H), 7.71 (dd, 1H), 7.54 (t, 2H), 7.44 (t, 1H), 7.41 (m, 4H), 7.36 (d, 2H), 7.16 (d, 2H), 6.67 (d, 1H), 5.22 (br, 2H), 3.55 (s, 3H); HPLC-MS calculated for C29H21ClN6O3S (M+H+) 569.1, found 569.1.

Provenance & Evidence