N,N-Dimethylaniline → HCID 22272855, compound

Participants

Reaction Steps

To a solution of 3-amino-2-(2-tert-butyldimethylsilyloxyethylthio)-6-methyl-4-methylthiopyridine (synthesized by the method disclosed in Example 30 in WO96/26925) (1.50 g, 4.35 mmol) in dichloromethane (30 ml) were added N,N-dimethylaniline (0.63 g, 5.22 mmol) and bromoacetyl bromide (1.05 g, 5.22 mmol) with ice-cooling and stirring, and the mixture was stirred at room temperature for 1 hour. The reaction solution was mixed with a saturated ammonium chloride solution and extracted with chloroform. The organic layer was washed with water and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (silica gel 100 g, developing solvent; hexane:ethyl acetate=3:1) to provide 1.57 g (yield 78%) of 2-bromo-N-[2-(2-tert-butyldimethylsilyloxyethylthio)-6-methyl-4-methylthio-3-pyridyl]acetamide as colorless powdery crystals.

Provenance & Evidence