Potassium Carbonate → 5-{[1-(2,5-dimethylphenyl)-3-(4-fluorophenyl)-1H-pyrazol-5-yl]amino}-2-(methylthio)pyrimidine-4-carboxylic acid

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Reaction Conditions

Reaction Steps

A mixture of 5-chloro-2-(methylthio)pyrimidine-4-carboxylic acid (89 mg, 0.44 mmol), potassium carbonate (66 mg, 0.48 mmol), 1-(2,5-dimethylphenyl)-3-(4-fluorophenyl)-1H-pyrazol-5-amine (123 mg, 0.44 mmol), synthesized in a similar manner as Intermediate G, and copper (II) acetate (1.6 mg, 0.009 mmol) in DMF (1 mL) was heated (150° C.) in a sealed tube for 16 h. The mixture was cooled to rt, filtered through a silica gel plug using ethyl acetate as eluent, concentrated to dryness, and subjected to HPLC purification using a gradient elution from 30% to 90% acetonitrile in water to afford 24.2 mg (12.3%) of the desired product. 1H NMR (300 MHz, CD2Cl2) δ 8.95 (s, 1H), 8.90 (s, 1H), 7.85 (dd, 2H), 7.10-7.28 (m, 5H), 7.62 (s, 1H), 2.58 (s, 3H), 2.38 (s, 3H), 2.14 (s, 3H); ES-MS m/z 406.3 (MH+-CO2), HPLC RT (min) 4.07.

Provenance & Evidence