Pyridine, hydrofluoride (1:1) → ((1R,4R)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopent-2-en-1-yl)methanol

Participants

Reaction Steps

To a solution of 7-[(1R,4R)-4-({[tert-butyl(dimethyl)silyl]oxy}-methyl)cyclopent-2-en-1-yl]-N-[(1S)-2,3-dihydro-1H-inden-1-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (81.9 mg, 0.178 mmol) in pyridine (0.800 mL) and THF (0.800 mL) at 0° C. under an atmosphere of nitrogen was added dropwise pyridine hydrofluoride (0.0500 mL, 0.555 mol). The solution was warmed to rt and stirred overnight. The reaction was quenched with saturated aqueous sodium bicarbonate solution and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 0 to 5% MeOH in DCM to afford the title compound as a white solid (˜70% purity, 35.7 mg, 41%). LC/MS: Rt=1.03 min, ES+ 347 (FA standard).

Provenance & Evidence