Cesium carbonate → HCID 57899372, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(4-chloro-phenyl)-1-(3-methanesulfonyl-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 (prepared as described in example 51, 0.60 g, 1.0 mmol) in N,N-dimethylformamide (20 mL) is degassed with argon for 0.5 h. Then 5-amino-2-bromopyridine (0.26 g, 1.5 mmol), cesium carbonate (0.648 g, 1.99 mmol), Pd(dppf)2Cl2 (0.073 g, 0.099 mmol is added and the resulted mixture is degassed with argon for 0.5 h. The reaction mixture is then heated at 100° C. for 12 h. The reaction mixture is cooled to rt and diluted with water and extracted with ethyl acetate (3×). The combined organic layer is washed with brine, dried over Na2SO4, concentrated, and purified by preparative HPLC to afford 6-[4-(5-amino-pyridin-2-yl)-phenyl]-5-(4-chloro-phenyl)-1-(3-methane-sulfonyl-phenyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one. 1H NMR (CD3OD, 400 MHz) δ 8.94 (m, 1H), 8.60 (m, 1H), 8.41 (s, 1H), 7.95-7.99 (m, 3H), 7.82 (t, 1H), 7.68-7.75 (m, 5H), 7.34-7.39 (m, 4H), 3.19 (s, 3H); LC-MS calculated for C29H21ClN6O3S (M+H+) 569.1, found 569.0.

Provenance & Evidence