反应详情

温度

85 °C

To a solution of N-(4-chlorophenyl)butyrimidamide (compound 3, 3.5 g, 17.80 mmol), NaHCO3 (3.14 g, 37.38 mmol) in i-PrOH was added ethyl bromopyruvate (compound 4, 4.7 mL, 37.38 mmol) under N2. The reaction mixture was stirred at 85° C. for 72 hrs, then added AcOH (15 mL). After 4 hrs, the mixture was concentrated under reduced pressure. The residue was diluted with H2O, and extracted with CH2Cl2. The organic layer was washed with saturated NaHCO3 and 1N-HCl solution, then dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (Biotage Isolera™ FLASH Purification System was used for normal phase column chromatography with EtOAc and hexane) to provide the title compound (1.28 g, 25%) as a brown oil.

1. waitAfter 4 hrs
2. concentrationthe mixture was concentrated under reduced pressure
3. additionThe residue was diluted with H2O
4. extractionextracted with CH2Cl2
5. washThe organic layer was washed with saturated NaHCO3 and 1N-HCl solution
6. dry with materialdried over anhydrous MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude product was purified by flash column chromatography (Biotage Isolera™ FLASH Purification System was used for normal phase column chromatography with EtOAc and hexane)