Pyrrolidine → Methyl 4-[4-methoxy-2-methyl-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyrimidine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

Dimedone (127 mg, 0.907 mol) and pyrrolidine (34.4 μL, 0.0412 mmol) were added to a suspension of the methyl 4-(3-formyl-4-methoxy-2-methylphenyl)pyrimidine-2-carboxylate obtained in Example 75-2 (118 mg, 0.412 mmol) in ethanol (2.0 mL) at room temperature, and the mixture thus obtained was then stirred at 80° C. for 1.5 hours. Thereafter, the reaction solution was cooled to room temperature, and the solvent was then distilled away under reduced pressure. The residue thus obtained was dissolved in chloroform (2.0 mL), and p-toluenesulfonic acid monohydrate (23.5 mg, 0.124 mmol) was then added to the solution thus obtained at room temperature. The mixture thus obtained was stirred at 70° C. for 1 hour. Thereafter, the reaction solution was cooled to room temperature, and a saturated aqueous solution of sodium hydrogen carbonate was then added to the reaction solution. The mixed solution was extracted with dichloromethane twice, and the organic layer thus obtained was then dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 0:1, v/v) to obtain the title compound (209 mg, yield: 95%).

Provenance & Evidence