Pyridine → HCID 58944580, compound

Participants

Reaction Conditions

Reaction Steps

2-((1S,2S,4R)-2-{[tert-Butyl(dimethyl)silyl]oxy}-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)ethyl sulfamate (0.0442 g, 0.0773 mmol) was dissolved in pyridine (0.344 mL, 4.25 mmol) and tetrahydrofuran (0.345 mL, 4.25 mmol). The solution was cooled to 0° C. Pyridine hydrofluoride (0.500 mL, 5.55 mmol) was added dropwise. The solution was warmed to room temperature. After one hour, pyridine hydrofluoride (0.500 mL, 5.55 mmol) was added. After two hours, pyridine hydrofluoride (0.500 mL, 5.55 mmol) was added. The solution was stirred for 24 h. The reaction was quenched with dropwise addition of saturated sodium bicarbonate, and the mixture was extracted with EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with 0 to 5% MeOH in EtOAc, to give the title compound (0.005 g, 0.01 mmol). 1H NMR (CD3OD, 400 MHz, δ): 8.17 (s, 1H), 7.28-7.12 (m, 5H) 6.67 (d, J=3.61 Hz 1H) 5.58 (t, J=7.44, 7.44 Hz 1H), 5.48-5.40 (m, 1H), 4.40-4.35 (m, 1H), 4.28-4.17 (m, 2H), 3.10-3.02 (m, 1H), 2.98-2.88 (m, 1H), 2.68-2.47 (m, 1H), 2.57-2.47 (m, 1H), 2.38-1.98 (m, 5H), 1.89-1.80 (m, 1H) ppm. LC/MS: Rt=1.25 min, ES+ 458 (FA standard).

Provenance & Evidence