Potassium Carbonate → 2-[(2-Nitrophenyl)sulfanyl]pyrimidine

Participants

Reaction Steps

A mixture of 2 mercaptopyrimidine (2.00 g, 17.8 mmol), 1-fluoro-2-nitrobenzene (2.50 g, 17.8 mmol) and potassium carbonate (2.46 g, 17.8 mmol) in DMF (15 mL) was stirred under reflux for 2 h. After removal of DMF, the residue was dissolved in DCM and washed with NaOH (5%, 3×20 mL) and brine. The organic layer was dried (MgSO4), filtered and evaporated to give 2-(2-nitro-phenylsulfanyl)-pyrimidine (3.45 g, 83%) as a yellow solid which was used in the next step without further purification. LC/MS (APCI) tr=3.66 min, m/z 379.28 (39), 233.98 (M++H, 100). HPLC tr=2.22 min (99.67%) 1H NMR (270 MHz, CDCl3) δ 7.03 (1H, t, J=4.7 Hz, Pyrimidine-H), 7.51-7.64 (2H, m, ArH), 7.80 (1H, dd, J=7.7, 1.5 Hz, ArH), 8.03 (1H, dd, J=7.7, 2.0 Hz, ArH) and 8.48 (2H, d, J=4.7 Hz, Pyrimidine-H).

Provenance & Evidence