Dimethylcarbamoyl Chloride → 5-Cyano-2-methylthiazolo[5,4-b]pyridine

Participants

Reaction Steps

To a solution of the product of Step 3 (4.706 g, 28.3 mmol) in 60 mL of CH2Cl2 was added trimethylsilyl cyanide (7.6 mL, 57 mmol) and the mixture was stirred at room temperature for 30 min. Dimethylcarbamyl chloride (5.2 mL, 56 mmol) was then added and the mixture was heated to reflux overnight. At 0° C., 2N NaOH (60 mL) was added and the mixture was stirred at this temperature one hour. The product was extracted in EtOAc, dried over Na2SO4, and purified by flash chromatography on silica with EtOAc: toluene 10:90; yield: 4.50 g, (91%).

Provenance & Evidence