Triethylamine → HCID 69433538, compound

Participants

Reaction Steps

(5-Hydroxymethylpyrimidin-2-yl)phenylcarbamic acid tert-butyl ester (286 mg, 0.949 mmol) obtained in Step 6 was dissolved in dichloromethane (10 mL), and triethylamine (0.265 mL, 1.90 mmol) and methanesulfonyl chloride (0.147 mL, 1.90 mmol) were added to the solution at 0° C., followed by stirring at room temperature for 2 hours. After the reaction was finished, the reaction mixture was added with methanol to decompose excess reagents, and the mixture was diluted with chloroform and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Then the residue was dissolved in DMF (10 mL), and the solution was added with 2-ethyl-5,7-dimethylimidazo[4,5-b]pyridine (234 mg, 1.34 mmol) and lithium hydroxide monohydrate (56.0 mg, 1.34 mmol) followed by stirring at 60° C. for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:1) to obtain [5-(2-ethyl-5,7-dimethylimidazo[4,5-b]pyridin-3-ylmethyl)pyrimidin-2-yl]phenylcarbamic acid tert-butyl ester (412 mg, 81%).

Provenance & Evidence