p-Toluenesulfonic acid → 1-(2-(2-(5-Chloro-2-(1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-ylamino)pyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide

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Reaction Steps

A stirred solution of 1-(2-(2-(2,5-dichloropyrimidin-4-yl)ethyl)phenyl)cyclopropanecarboxamide A14 (0.085 g, 0.25 mmol), 1-(1-methylpyrrolidin-3-yl)-1H-pyrazol-4-amine A24 (0.046 g, 0.278 mmol) and TsOH (0.003 g, 0.02 mmol) in 1,4-dioxane (4 mL) was stirred at 120° C. in the microwave for 60 minutes followed by 150° C. for 2 hours and then 160° C. for 2 hours. After cooling, the solvent was removed to afford a crude red oil that was purified by flash chromatography (0-30% MeOH in DCM) followed by HPLC (Gradient: 20-100%, Acetonitrile 0.1% formic acid in water 0.1% formic acid, 12 min) to give the title compound 21 as a clear gum (0.008 g, 7% yield). LCMS-C: rt 4.34 min; m/z 466 [M+H]+.

Provenance & Evidence