Methanol → HCID 86669032, compound

Participants

Reaction Steps

To a solution of 3,5-dichloro-4-[4-(6-methylpyrimidin-4-ylamino)-thiazolo[5,4-c]pyridin-2-yl]benzonitrile (54 mg, 0.12 mmol) in MeOH (3 mL) was added a solution of sodium methoxide in methanol (0.054 mL, 0.24 mmol) and the reaction mixture was stirred at room temperature for 48 hours. After this time, an additional portion of sodium methoxide in methanol (0.0082 mL, 0.14 mmol) was added, stirred for 1 hour and then ammonium chloride (7.0 mg, 7.1 mmol) was added and the resultant mixture was heated at reflux overnight. After cooling to room temperature, additional ammonium chloride (11.4 mg, 0.21 mmol) was added and heated at reflux for a further 5 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resultant residue was purified by reverse phase HPLC (Phenomenex Gemini 5 μm C18 on a 25 minute gradient 5-50%, 0.1% HCO2H in CH3CN/H2O) to afford the title compound (5.6 mg, 10% yield) as yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.75 (br s, 1H), 9.60 (s, 2H), 9.34 (s, 2H), 8.61 (s, 1H), 8.42 (d, J=5.5 Hz, 1H), 8.14 (s, 2H), 7.82 (d, J=5.3 Hz, 1H), 7.54 (s, 1H), 2.41 (s, 3H). LCMS (Method C): RT=2.06 min, m/z: 412 [M+H+].

Provenance & Evidence