Cesium carbonate → 3,5-Dichloro-4-[4-(2,6-dimethylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]benzonitrile

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Reaction Conditions

Reaction Steps

A suspension of 3,5-dichloro-4-(4-chloropyrazolo[4,3-c]pyridin-2-yl)benzonitrile (65 mg, 0.20 mmol), 4-amino-2,6-dimethylpyrimidine (27 mg, 0.22 mmol), Pd2(dba)3 (5 mg, 0.005 mmol), Xantphos (12 mg, 0.02 mmol) and cesium carbonate (91 mg, 0.28 mmol) in dioxane (2 mL) was sealed in a reaction vial, purged with nitrogen, and heated at 90° C. for 18 hours. The reaction mixture was cooled, filtered, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (30-100% ethyl acetate in cyclohexane), then by HPLC (gradient: 25 to 98% acetonitrile in water with 0.1% ammonium hydroxide), to afford the title compound as a white solid (22 mg, 27% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.41 (d, J=0.9 Hz, 1H), 8.51 (s, 2H), 8.08 (d, J=6.9 Hz, 1H), 7.67 (s, 1H), 7.54 (dd, J=6.9, 1.0 Hz, 1H), 2.73 (s, 3H), 2.58 (s, 3H). LCMS (Method B): RT=3.00 min, m/z: 410.15 [M+H+].

Provenance & Evidence