Dimethylformamide → N-tert-butyl-5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxamide

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Reaction Steps

In a 2 mL flask, 5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxylic acid (6.5 mg, 0.020 mmol) and HATU (9.2 mg, 0.024 mmol) were dissolved in DMF (101 μL, 0.020 mmol). After 5 minutes, 2-methylpropan-2-amine (4.4 mg, 0.061 mmol) and diisopropylethylamine (11 μL, 0.061 mmol) were added and the reaction mixture stirred at ambient temperature for 45 minutes. The reaction mixture was diluted in EtOAc and washed with water, saturated sodium bicarbonate, water and brine. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by reverse phase HPLC using a gradient of 40-100% acetonitrile/water to afford N-tert-butyl-5-(1-(2-cyano-1-cyclopropylethyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine-7-carboxamide (1.0 mg, 0.0026 mmol, 13% yield). MS (apci) m/z=378.3 (M+H).

Provenance & Evidence