HCID 86614252, compound → HCID 58944608, compound

Participants

Reaction Steps

((1S,2S,4R)-2-{[tert-Butyl(dimethyl)silyl]oxy}-4-{4-[(cyclopropylmethyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methyl sulfamate (88.0 mg, 0.178 mmol) was dissolved in THF (1.00 mL) and pyridine (3.00 mL). Pyridine hydrofluoride (12 drops) was added and the reaction was stirred for 3 h. The reaction was quenched using saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with EtOAc (3×10 mL), and the combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 5% MeOH in DCM. The compound was re-purified via silica gel chromatography eluting with 10% MeOH in DCM to afford the title compound (3.00 mg, 4.4%). 1H NMR (400 MHz, CD3OD, δ): 8.05 (s, 1H), 7.15 (d, J=3.6 Hz, 1H), 6.59 (d, J=3.6 Hz, 1H), 5.45-5.32 (m, 1H), 4.56 (br s, 1H), 4.45 (br s, 1H), 4.33 (dd, J=7.6, 7.6 Hz, 1H), 4.15 (dd, J=7.4, 7.4 Hz, 1H), 3.34 (d, J=6.9 Hz, 2H), 2.83-2.68 (m, 1H), 2.35-2.08 (m, 3H), 2.05-1.93 (m, 1H), 1.33-1.03 (m, 3H), 0.93-0.77 (m, 1H) ppm. LC/MS: Rt=0.85 min, ES+ 382 (FA standard).

Provenance & Evidence