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

HRID 1440451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1440451
[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-5yl)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-fb0415ddffe3422eb16e8c9c48896a82
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05498776

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