Chloroacetaldehyde → HCID 58654351, compound

Participants

Reaction Steps

Potassium carbonate (700 mg, 5.20 mmol) and 2-chloroacetaldehyde (400 mg, 5.20 mmol) were added sequentially to a solution of 2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-3-thiocarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester (400 mg, 1.04 mmol) in DME (10 mL) at rt under an atmosphere of N2. The reaction mixture was stirred at room temperature for 16 h then filtered under vacuum. The filtrate was concentrated and the residue dissolved in DME (10 mL) prior to cooling to 0° C. Trifluoroacetic anhydride (655 mg, 3.12 mmol) and pyridine (575 mg, 7.28 mmol) were added and reaction mixture was stirred at rt for 4 h. The mixture was concentrated and the residue was diluted with DCM (20 mL). The solution was washed with water (2×30 mL), dried over Na2SO4, filtered and concentrated. The crude product was purified using column chromatography (DCM to 9:1 DCM/MeOH) to afford 2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-3-thiazol-2-yl-pyrrolidine-1-carboxylic acid tert-butyl ester as a yellow oil (200 mg, 50%).

Provenance & Evidence