Methyl iodide → 1,3-Dimethyl-6-(trifluoromethyl)uracil

HRID 844868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 844868
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]([F:12])([F:11])[F:10])[NH:4][C:3]1=[O:13].[C:14](=O)([O-])[O-].[K+].[K+].CI>COCCOC.O>[CH3:14][N:4]1[C:5]([C:9]([F:10])([F:12])[F:11])=[CH:6][C:7](=[O:8])[N:2]([CH3:1])[C:3]1=[O:13]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21824424HCID 21824424, Verbindung

Produkt 1

HCID 27586691,3-Dimethyl-6-(trifluoromethyl)uracilAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a suspension of 3-methyl-6-(trifluoromethyl)uracil (20.6 mmol, 4.0 g) and powdered potassium carbonate (41.2 mmol, 5.7 g) in DME (30 mL) was added methyl iodide (82.4 mmol, 5.13 mL). Then, the reaction mixture was refluxed for 4 h at which time the TLC analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was cooled to room temperature and was diluted with water (50 mL). Then, the DME was removed under reduced pressure to afford a white suspension. The solids were collected by filtration and washed with water. After air drying, 3.55 g (83% yield) of 1,3-dimethyl-6-(trifluoromethyl)uracil was obtained as a white solid: mp 85-87° C. EI-HRMS m/e calcd for C7H7F3N2O2 (M+) 208.0459, found 208.0460.

Aufarbeitung

  1. temperatureThen, the reaction mixture was refluxed for 4 h at which time the TLC analysis of the reaction mixture
  2. customThen, the DME was removed under reduced pressure
  3. customto afford a white suspension
  4. filtrationThe solids were collected by filtration
  5. washwashed with water
  6. customAfter air drying

Quellen und Nachweise

ORD-Eintrag
ord-f382435a286f431d9a83f4087f6cebac
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06380387B1

Notizen zur Reaktion

Wird geladen…