Réaction #162818

Équation de réaction

1,3-diphenyl-pyrimidine-2,4,6-trione

Phosphorus oxychloride

→

6-chloro-1,3-diphenyl-1H-pyrimidine-2,4-dione

Rendement 74.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAfter the completion of the dropwise addition
2. 2
   workup.STIRRINGthe mixture was stirred
3. 3
   Températureunder heating at 110° C. for 3 hrs
4. 4
   Températureto cool to room temperature
5. 5
   workup.STIRRINGthe mixture was stirred at room temperature
6. 6
   Extractionextracted with ethyl acetate
7. 7
   LavageThe organic layer was washed with brine and saturated aqueous sodium hydrogen carbonate
8. 8
   Séchagedried over anhydrous sodium sulfate. Anhydrous sodium sulfate
9. 9
   Filtrationwas filtered off
10. 10
    Concentrationthe filtrate was concentrated under reduced pressure
11. 11
    AutreThe residue was purified by column chromatography (hexane:ethyl acetate=2:1→3:2)

Mode opératoire

To 1,3-diphenyl-pyrimidine-2,4,6-trione 19 (78.0 g) obtained in Step 1 was added water (16 ml). Phosphorus oxychloride (422 ml) was added dropwise under stirring at room temperature over 50 min. After the completion of the dropwise addition, the mixture was stirred under heating at 110° C. for 3 hrs. After allowing to cool to room temperature, the reaction mixture was added to ice water by small portions and the mixture was stirred at room temperature and extracted with ethyl acetate. The organic layer was washed with brine and saturated aqueous sodium hydrogen carbonate, and dried over anhydrous sodium sulfate. Anhydrous sodium sulfate was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (hexane:ethyl acetate=2:1→3:2) to give 6-chloro-1,3-diphenyl-1H-pyrimidine-2,4-dione 20 (61.5 g, yield 74%) as pale-yellow crystals.

Source