Phosphorus oxychloride → Ethyl 3-(4-Chloro-2,6-dimethylpyrimidin-5-yl)propionate

HRID 1886060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1886060
[CH3:1][C:2]1[NH:7][C:6](=O)[C:5]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([CH3:16])[N:3]=1.P(Cl)(Cl)([Cl:19])=O>CN(C)C1C=CC=CC=1>[Cl:19][C:6]1[C:5]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:4]([CH3:16])[N:3]=[C:2]([CH3:1])[N:7]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 1359679873-(4-Hydroxy-2,6-dimethyl-pyrimidin-5-yl)-propionic acid ethyl ester

Produkt 1

HCID 14916837Ethyl 3-(4-Chloro-2,6-dimethylpyrimidin-5-yl)propionateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 949N,N-DimethylanilineKatalysator

Versuchsvorschrift

A mixture of ethyl 3-(2,6-dimethyl-3H-pyrimidin-4-on-5-yl)propionate (3.87 g, 0.017 mol), phosphorus oxychloride (40 mL), and N,N-dimethylaniline (10 drops) was heated under reflux for 2 h. The mixture was concentrated, cooled, and ice water was added. Solid KOH was added to bring the pH to 6 and the mixture was extracted with ether. The extracts were dried (MgSO4) and concentrated to give 2.95 g (72%) of product as a brown oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. concentrationThe mixture was concentrated
  4. temperaturecooled
  5. additionice water was added
  6. additionSolid KOH was added
  7. extractionthe mixture was extracted with ether
  8. dry with materialThe extracts were dried (MgSO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-71bd02bd9bb64052b97b155d23f72207
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05149699

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