4-Nitrophenol → HCID 58938019, compound

Participants

Reaction Steps

To a stirred slurry of 6-chloro-9-(tetrahydro-pyran-2-yl)-9H-purine (2.3 g, 10 mmol, 3 equiv) in anhydrous 1,2-dichloroethane (60 mL) was added a solution of 4-nitrophenol (2.3 g, 10 mmol, 3 equiv), DABCO (1.12 g, 1 mmol, 1 equiv) and triethylamine (3.03 g, 4.18 mL, 3 mmol, 3 equiv) in anhydrous 1,2-dichloroethane (5 mL). The mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with DCM (25 mL), washed with saturated solution of NaHCO3. The aqueous layer was re-extracted with DCM. The combined organic extracts were dried over MgSO4, filtered followed by solvent evaporation, giving 6-(4-nitro-phenoxy)-9-(tetrahydro-pyran-2-yl)-9H-purine (4 g, >99% yield). 1H NMR (400 MHz, CDCl3): δ 8.6 (s, 1H), 8.3 (m, 2H), 8.25 (s, 1H), 7.60 (m, 2H), 5.8 (m, 1H), 4.20 (m, 1H), 3.8 (m, 1H), 2.20 (m, 3H), 1.80 (m, 3H). MS (ESI) for C16H15N5O4: 342 (MH+).

Provenance & Evidence