Phosphorus oxychloride → Ethyl 5-chloropyrazolo(1,5-a)pyrimidine-3-carboxylate

HRID 1631294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1631294
O[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]2[N:3]=1.P(Cl)(Cl)([Cl:18])=O>>[Cl:18][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]2[N:3]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178469952HCID 178469952, Verbindung

Produkt 1

HCID 58063474Ethyl 5-chloropyrazolo(1,5-a)pyrimidine-3-carboxylateAusbeute 97,6 %

Versuchsvorschrift

Ethyl 5-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate (22.7 g, 110 mmol) was suspended in phosphoryl trichloride (100 mL) and heated to reflux. After heating for 2 hours, the reaction mixture was cooled and concentrated to remove the excess POCl3. The residue was diluted in DCM (100 mL) and slowly added to a flask containing ice water. The mixture was separated and the aqueous layer extracted with DCM. The combined organics were dried with MgSO4, filtered and concentrated to afford ethyl 5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (24.2 g, 97.6% yield) as a pale yellow solid. MS (apci) m/z=225.9 (M+H).

Aufarbeitung

  1. temperatureheated to reflux
  2. temperatureAfter heating for 2 hours
  3. temperaturethe reaction mixture was cooled
  4. concentrationconcentrated
  5. customto remove the excess POCl3
  6. additionThe residue was diluted in DCM (100 mL)
  7. additionslowly added to a flask
  8. additioncontaining ice water
  9. customThe mixture was separated
  10. extractionthe aqueous layer extracted with DCM
  11. dry with materialThe combined organics were dried with MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6a5c1bdf4ef6439e85fe185602ab8d21
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791123B2

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