Pyridine → (1S,2S,4R)-4-{4-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-(hydroxymethyl)cyclopentyl acetate

Participants

Reaction Steps

(1S,2S,4R)-2-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl acetate (3.66 g, 7.03 mmol) was dissolved in THF (31.3 mL) and pyridine (31.3 mL, 387 mmol) in a polypropylene vial and the solution was cooled to 0° C. Pyridine hydrofluoride (8.61 mL, 95.6 mmol) was added dropwise and the mixture was stirred at rt for 1 hour. The resulting solution was added dropwise into a solution of saturated aqueous sodium bicarbonate (150 mL), extracted with EtOAc (3×50 mL), dried with MgSO4, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography eluting with a gradient of 0 to 10% MeOH in DCM to afford the title compound (2.30 g, 80%). LC/MS: Rt=1.64 min, ES+ 407 (AA standard).

Provenance & Evidence