Acetaldehyde → 2-(2-(2-(2-((1-(1-Ethylpiperidin-4-yl)-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide

Participants

Reaction Steps

Acetaldehyde (17 μL, 0.31 mmol) was added to a solution of 2-(2-(2-(2-((1-(piperidin-4-yl)-1H-pyrazol-4-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)ethyl)phenyl)propanamide A67 (50 mg, 0.10 mmol) in EtOH (20 mL). After 10 minutes, NaHB(OAc)3 (86 mg, 0.41 mmol) was added and the mixture was stirred for 3 hours. The reaction was quenched with water (20 mL) and the volatiles were removed in vacuo. The resultant solid was suspended in water (25 mL), sonicated for 10 minutes, collected by filtration and then dissolved in acetone (3 mL). Addition of petroleum benzine 40-60° C. gave a precipitate that was collected by filtration to give the title compound 59 as a tan solid (42 mg, 79%). LCMS-A: rt 4.808 min; m/z 516.3 [M+H]+.

Provenance & Evidence