Cesium carbonate → HCID 25054172, compound

Participants

Reaction Steps

5-Methyl-2-(6-methylsulfanyl-pyrimidin-4-yl)-2H-pyrazol-3-ylamine (90 mg, 0.40 mmol) is mixed with N-(3-Bromo-4-methyl-phenyl)-3-trifluoromethyl-benzamide (228 mg, 0.64 mmol), palladium acetate (20 mg, 0.089 mmol), Xantophos (75 mg, 0.13 mmol) and cesium carbonate (420 mg, 1.28 mmol). 4 mL anhydrous 1,4-dioxane is added under a nitrogen environment and the mixture is subjected to microwave irradiation to 150° C. for 30 minutes. The reaction mixture is then cooled to room temperature, treated with 100 mL THF, passed through a celite column and concentrated. The crude product is purified by ISCO chromatography eluting with ethyl acetate in hexanes from 0% to 40% to afford N-{4-Methyl-3-[5-methyl-2-(6-methylsulfanyl-pyrimidin-4-yl)-2H-pyrazol-3-ylamino]-phenyl}-3-trifluoromethyl-benzamide: 1H NMR 400 MHz (d6-DMSO) δ 10.65 (s, 1H), 10.46 (s, 1H), 8.89 (s, 1H), 8.30-8.25 (m, 2H), 7.98 (d, J=7.5 Hz, 1H), 7.89 (s, 1H), 7.80 (t, J=7.5 Hz, 1H), 7.67 (s, 1H), 7.40 (d, J=7.5 Hz, 1H), 7.25 (d, J=8.2 Hz, 1H), 6.12 (s, 1H), 2.61 (s, 3H), 2.34 (s, 3H), 2.25 (s, 3H); MS m/z 499.14 (M+1).

Provenance & Evidence