Aniline → HCID 23156191, compound

Participants

Reaction Steps

Ethyl 2-(methylthio)pyrimidine-5-carboxylate (0.800 g, 4.03 mmol) obtained in Step 1 was dissolved in dichloromethane (40 mL), and m-chloroperbenzoic acid (1.61 g, 6.06 mmol) was added to the solution, followed by stirring at room temperature for 1 hour. After the reaction mixture was diluted with dichloromethane, the dilute solution was washed with a saturated aqueous sodium hydrogen carbonate solution and water, and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in dioxane (20 mL), and the solution was added with aniline (0.730 mL, 8.01 mmol) followed by stirring at 90° C. for 6 hours. After the reaction mixture was diluted with an aqueous (+)-potassium sodium tartrate solution and ethyl acetate, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3) to obtain ethyl 2-(phenylamino)pyrimidine-5-carboxylate (0.871 g, 89%).

Provenance & Evidence