Triethylamine → HCID 90051807, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(benzyloxy)-2-(methylthio)pyrimidine-5-carbaldehyde oxime (S21, 705 mg) in N,N-dimethylformamide (6.0 mL), pyridine (20.6 μL) and N-chlorosuccinimide (471 mg) were added under ice cooling, and the mixture was stirred at 50° C. for 1 hour. The reaction mixture was cooled to room temperature, then a solution of N-(3-butynyl)phthalimide (765 mg) and triethylamine (603 μL) in tetrahydrofuran (8.5 mL) was added to the reaction mixture, and the mixture was stirred at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 2-(2-(3-(4-(benzyloxy)-2-(methylthio)pyrimidin-5-yl)isoxazol-5-yl)ethyl)isoindoline-1,3-dione (S22, 439 mg).

Provenance & Evidence