Phosphorus oxychloride → Ethyl 3-(4-Chloro-6-methyl-2-methoxymethylpyrimidin-5-yl)propionate

HRID 129008

Reaktionsgleichung

Reaktionsgleichung von HRID 129008
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][O:9][CH3:10])[NH:5][C:4](=O)[C:3]=1[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:4]1[C:3]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:2]([CH3:1])[N:7]=[C:6]([CH2:8][O:9][CH3:10])[N:5]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 136067006Ethyl 3-(6-Methyl-2-methoxymethyl-3H-pyrimidin-4-on-5-yl)propionate

Produkt 1

HCID 19372999Ethyl 3-(4-Chloro-6-methyl-2-methoxymethylpyrimidin-5-yl)propionateAusbeute 84 %

Versuchsvorschrift

A mixture of ethyl 3-(6-methyl-2-methoxymethyl-3H-pyrimidin-4-on-5yl)propionate (4.00 g, 15.6 mmol) and phosphorus oxychloride (25 mL) was heated under reflux for 2 h. The mixture was concentrated, cooled, and poured onto ice. 1N NaOH was added to bring the pH to 6 and the mixture was extracted with EtOAc. The extracts were dried (MgSO4) and concentrated to give 3.6 g (84%) of product as a brown oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. concentrationThe mixture was concentrated
  4. temperaturecooled
  5. additionpoured onto ice
  6. addition1N NaOH was added
  7. extractionthe mixture was extracted with EtOAc
  8. dry with materialThe extracts were dried (MgSO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c6880a16509d4865bfbafe2f1f73db59
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466692

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