Cesium carbonate → {6-[7-Chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamino]-pyrimidin-4-yl}-methanol

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Reaction Steps

A suspension of 4-bromo-7-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine (200 mg, 0.53 mmol), (6-amino-pyrimidin-4-yl)-methanol (73 mg, 0.58 mmol), Pd2(dba)3 (24 mg, 0.025 mmol), Xantphos (31 mg, 0.05 mmol) and cesium carbonate (347 mg, 1.1 mmol) in dioxane (3 mL) was sealed in a microwave vial, purged with nitrogen, and irradiated in a microwave reactor at 150° C. for 30 min. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by NH2 silica gel flash chromatography (0-2% methanol in ethyl acetate), to afford the title compound as a pale yellow solid (57 mg, 34% yield). 1H (400 MHz, DMSO-d6+d-TFA): δ 9.36 (s, 1H), 9.04 (s, 1H), 8.27 (bs, 1H), 8.16 (s, 1H), 7.80 (d, J=1.2 Hz, 1H), 7.78 (s, 1H), 7.70 (dd, J=9.0, 7.3 Hz, 1H), 4.67 (s, 2H). LCMS (Method B): RT=3.19 min, m/z: 421 [M+H+].

Provenance & Evidence