1,2-Dichloroethane → HCID 89580281, compound

Participants

Reaction Steps

2-(4-(4-fluorophenoxy)phenyl)-6-vinylpyrimidine-4-carboxylic acid (23) (580 mg, 1.73 mmol), HOBt (279.5 mg, 2.07 mmol), and EDC (395.4 mg, 2.07 mmol) in dry dichloromethane were stirred for 20 minutes at room temperature and MeOH (3.46 mL, 86.5 mmol) was added thereto. After the reaction was complete, the solvent was removed in vacuo. The residue was dissolved in dichloromethane which was then washed with H2O. The organic layer was dried over anhydrous MgSO4 and concentrated to give oily residue. The resulting oil was purified by Combiflash (50% EtOAc in Hexanes) to give methyl 2-(4-(4-fluorophenoxy)phenyl)-6-vinylpyrimidine-4-carboxylate (24) (568 mg, 94% yield). 1H NMR (400 MHz, CD3OD): 8.45 (2H, d, J=8.5 Hz), 7.74 (1H, s), 6.90-7.01 (6H, m), 6.77-6.86 (1H, dd, J=11, 18 Hz), 6.60 (1H, d, J=17 Hz), 5.7 (1H, d, J=10.5 Hz), 3.98 (3H, s); LC/MS: m/z=351[M+H]+.

Provenance & Evidence