Triethylamine → N-methoxy-N-methyl-5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxamide

Participants

Reaction Steps

To a suspension of 5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid (2.15 g, 5.26 mmol) in dichloromethane (60 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.27 g, 13.0 mmol), N,O-dimethylhydroxylamine hydrochloride (2.49 g, 13.0 mmol), and triethylamine (2.30 g, 22.7 mmol) at 0° C. After being stirred for 17 h at room temperature, the reaction mixture was poured into saturated sodium bicarbonate. The mixture was extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate, filtrated and concentrated in vacuo. The crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=19:1) to give N-methoxy-N-methyl-5-pyrrolidin-1-yl-7-(tetrahydro-2H-pyran-4-ylamino)pyrazolo[1,5-a]pyrimidine-2-carboxamide. MS (APCI): m/z 375 (M+H).

Provenance & Evidence