Dimethylformamide → Methyl 5,6-dichloro-3-methylpyrazine-2-carboxylate

Participants

Reaction Steps

To a solution of 5-chloro-3-(methoxycarbonyl)-2-methylpyrazine 1-oxide (8.83 g, 43.6 mmol) in toluene (100 mL) at 0° C. was added phosphorus oxychloride (10 ml, 109 mmol) and DMF (1 ml, 12.91 mmol). The reaction mixture was stirred at room temperature for 1 h, and then was heated to 85° C. fort 8 h. The mixture was cooled to RT and concentrated. The residue was diluted with EtOAc and washed with saturated NaHCO3 solution. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude mixture was purified with ISCO (0% to 10% EtOAc/Hexanes) to afford the desired methyl 5,6-dichloro-3-methylpyrazine-2-carboxylate (6.51 g, 68% yield). 1H NMR (300 MHz, CDCl3) δ ppm 4.00 (3H, s), 2.83 (3H, s)

Provenance & Evidence