Ammonium formate → HCID 58938018, compound

Participants

Reaction Steps

To a round bottom flask equipped with a magnetic stir bar was added 6-(4-nitro-phenoxy)-9-(tetrahydro-pyran-2-yl)-9H-purine (4 g, 12.86 mmol, 1.0 eq.), 5% PtS (20% by weight, 800 mg), ammonium formate (3.2 g, 51.44 eq), and ethanol (100 ml). The reaction was stirred at reflux for 30 min upon which the reaction was filtered hot through celite. Removal of the ethanol was followed by the addition of 1N HCl, which was further washed twice with DCM (50 ml). The aqueous layer was basified and extracted with DCM. The organic layer was then washed twice with brine (50 ml) and dried over sodium sulfate. After removal of the DCM in vacuo, 4-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yloxy]-phenylamine was obtained (3 g, 83%) as a solid. 1H NMR (400 MHz, CDCl3): δ 8.4 (s, 1H), 8.2 (s, 1H), 7.0 (m, 2H), 6.75 (m, 2H), 5.8 (m, 1H), 4.20 (m, 1H), 4.0 (m, 2H), 3.8 (m, 1H), 2.20 (m, 3H), 1.80 (m, 3H). MS (ESI) for C16H17N5O2: 312 (MH+).

Provenance & Evidence