2,2,2-Trifluoroethanol → 2-Methylthio-4-(2,2,2-trifluoroethoxy)pyrimidine

HRID 916

Reaktionsgleichung

Reaktionsgleichung von HRID 916
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:16][C:17]([F:21])([F:20])[CH2:18][OH:19]>CN(C=O)C.O>[CH3:9][S:8][C:4]1[N:3]=[C:2]([O:19][CH2:18][C:17]([F:21])([F:20])[F:16])[CH:7]=[CH:6][N:5]=1

Komponenten

6

Edukt 3

HCID 64092,2,2-TrifluoroethanolHCID 11430Potassium CarbonateHCID 971134-Chloro-2-methylthiopyrimidine

Produkt 1

HCID 196941862-Methylthio-4-(2,2,2-trifluoroethoxy)pyrimidineAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 4-chloro-2-methylthiopyrimidine (16.0 g) and potassium carbonate (27.6 g) in DMF (90 ml) at 0° C., was added with stirring a solution of 2,2,2-trifluoroethanol (10.0 g) in DMF (10 ml). Stirring was continued for 64 hours, then the reaction mixture was diluted with water and extracted with ether (3×150 ml). The combined extracts were washed with brine, dried and concentrated to give 2-methylthio-4-(2,2,2-trifluoroethoxy)pyrimidine (23.0 g, crude yield) as a clear pale orange oil, 1H NMR δ 2.57(3H,s); 4.79(2H,q); 6.54(1H,d); 8.33(1H,d) ppm.

Aufarbeitung

  1. extractionextracted with ether (3×150 ml)
  2. washThe combined extracts were washed with brine
  3. customdried
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-95ae114a7a1047af99591a70a44e39c6
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723471

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