2,4-Dichloro-5-fluoropyrimidine → 2-Chloro-4-(1-ethoxyvinyl)-5-fluoropyrimidine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,4-dichloro-5-fluoro-pyrimidine (5.2 g, 31.14 mmol) in DMF (60 mL) was added tributyl-(1-ethoxy-vinyl)-stannane (12.37 g, 361.2 mmol), followed by dichlorobis(triphenylphosphine) palladium(II) (0.438 g, 0.623 mmol). The mixture was heated at 75° C. for 2 hours, cooled to rt and concentrated. The oily residue was dissolved in ethyl ether and a saturated solution of aqueous potassium fluoride was added and the mixture was stirred at room temperature for 18 hours. After dilution with EtOAc and filtration through Celite, the organic phase was washed with water, brine and concentrated. The crude material was purified by CombiFlash (0 to 10% EtOAc/Hex) to give desired product. LCMS-ESI+: calc'd for C8H9ClFN2O: 203.0 (M+H+); Found: 203.1 (M+H+); 1H NMR (400 MHz, Chloroform-d) δ 8.45 (d, J=2.8 Hz, 1H), 5.30 (d, J=3.1 Hz, 1H), 4.71 (d, J=3.1 Hz, 1H), 3.96 (q, J=7.0 Hz, 2H), 1.42 (t, J=7.0 Hz, 3H).

Provenance & Evidence