Sodium borohydride → HCID 69671881, compound

Participants

Reaction Steps

To a solution of 3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-formylbenzonitrile (24 mg, 0.06 mmol) in ethanol (IMS grade, 2.0 mL) and THF (2.0 mL) was added sodium borohydride (4 mg, 0.1 mmol) and the reaction mixture was stirred at room temperature for 2 hours. The resultant mixture was partitioned between ethyl acetate and water and the layers were separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with diethyl ether and the solid obtained was filtered and dried. This was then purified by silica gel flash chromatography (0-1% methanol in ethyl acetate) to afford the title compound as a white solid (4.0 mg, 16% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.82 (s, 1H), 9.46 (d, J=2.6 Hz, 1H), 8.71 (d, J=1.2 Hz, 1H), 8.38 (s, 1H), 8.09 (m, 2H), 8.03 (d, J=3.5 Hz, 1H), 5.76 (t, J=5.8 Hz, 1H), 4.71 (d, J=5.8 Hz, 2H), 2.46 (s, 3H). LCMS (Method B): RT=2.78 min, m/z: 410 [M+H+].

Provenance & Evidence