Pyridine → Phenyl 5-cyanopyrazin-2-ylcarbamate

Participants

Reaction Steps

A solution of Example 1B (6.0 g, 50 mmol) in a mixture of dichloromethane (100 mL) and THF (200 mL) in a room temperature water bath was treated with pyridine (4.45 mL, 55 mmol), treated dropwise with phenyl chloroformate (10.0 mL, 80 mmol), and stirred at room temperature overnight. The mixture was treated with ethyl acetate (500 mL) and filtered. The filter cake was washed with ethyl acetate and the combined filtrates were washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was triturated with 30% ethyl acetate/hexanes to provide 8.50 g (70.8%) of the desired product. MS (APCI(+)) m/z 241 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 11.76 (s, 1H), 9.20 (s, 1H), 8.98 (s, 1H), 7.20–7.50 (m, 5H).

Provenance & Evidence