Water → HCID 86679610, compound

Participants

Reaction Steps

A reaction vial was charged with 5-fluoro-N-(1-methyl-1H-pyrazol-3-yl)-4-(3-nitrophenoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (520 mg, 1.04 mmol), zinc dust (340 mg, 5.2 mmol), ammonium chloride (279 mg, 5.2 mmol), water (4 mL) and EtOAc (20 mL). The reaction mixture was capped and stirred at rt for 20 hrs. The reaction was diluted with EtOAc (100 mL) and saturated aqueous NaHCO3 (15 mL). The insoluble material was removed by filtration through Celite. The filtrate was separated, and the organic layer was washed with brine (10 mL), dried over Na2SO4 and evaporated to afford the title compound (394 mg, 81% yield) as a foam. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.52 (s, 1H) 7.45 (s, 1H) 7.26 (d, J=2.27 Hz, 1H) 7.14 (t, J=7.93 Hz, 1H) 6.49-6.59 (m, 2H) 6.46 (dd, J=7.93, 1.38 Hz, 1H) 6.30-6.43 (m, 1H) 5.50 (s, 2H) 5.32 (s, 2H) 3.75 (s, 3H) 3.56-3.67 (m, 2H) 0.89-0.98 (m, 2H) 0.00 (s, 9H). m/z (APCI+) for C22H28FN7O2Si 470.1 (M+H)+.

Provenance & Evidence