Acetonitrile → Sodium 3-cyano-1-(2,6-difluorophenyl)-6-oxo-1,6-dihydropyridine-2-thiolate

Participants

Reaction Steps

A solution of sodium bis(trimethylsilyl)amide (351 ml of a 1M solution in THF, 351 mmol) in THF (150 ml) was cooled to −78° C. and acetonitrile (30 ml) was added. After 20 min, 2,6-difluorophenyl isothiocyanate (30.0 g, 175.5 mmol) was added slowly over 5 min. The reaction mixture was allowed to warm slowly to r.t. over 2 h. EtOH (100 ml) was added followed by 1,3-dimethyluracil (27.0 g, 193.5 mmol) and the mixture heated to reflux for 18 h. After cooling, the mixture was concentrated in vacuo to a volume of approx. 150 ml and EtOH (75 ml) was added. This mixture was cooled and Et2O (approx. 750 ml) was added slowly to give a pale yellow precipitate. The solid was filtered off, washed with Et2O (2×100 ml) then dried to give the title compound as a yellow/pale brown solid (49.0 g, 86%). δH (DMSO-d6) 7.43-7.33 (1H, m), 7.23 (1H, d, J 9.2 Hz), 7.13-7.06 (2H, m), 5.64 (1H, d, J 9.2 Hz). LCMS (ES+) RT 7.0 minutes, 265 (M+H)+.

Provenance & Evidence