Ethyl Acetate → 4-Chloro-5-(2,4-difluorophenoxy)-2-methylsulfanylpyrimidine

HRID 575630

Reaktionsgleichung

Reaktionsgleichung von HRID 575630
[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[C:6](O)=[N:7][C:8]([S:11][CH3:12])=[N:9][CH:10]=1.O=P(Cl)(Cl)[Cl:21].CC(=O)OCC>[N+](C)(C)(C)C.[Cl-].CC#N>[Cl:21][C:6]1[C:5]([O:4][C:3]2[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:2]=2[F:1])=[CH:10][N:9]=[C:8]([S:11][CH3:12])[N:7]=1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 1785034745-(2,4-Difluorophenoxy)-2-methylsulfanylpyrimidin-4-ol

Produkt 1

HCID 1180215104-Chloro-5-(2,4-difluorophenoxy)-2-methylsulfanylpyrimidineAusbeute 70,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6379Tetramethylammonium chlorideKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

The title compound of step 1 (5.30 g, 19.63 mmol), POCl3 (18.06 g, 117.78 mmol), (Me)4NCl (3.23 g, 29.47 mmol) in dry CH3CN (60 mL) was refluxed for 12 h. The mixture was poured into ice-water (50 mL) and subjected to EA extractive work up. Concentration under vacuum gave impure title compound (4.0 g), which was carried on to the next step.

Aufarbeitung

  1. concentrationConcentration under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2f82fdc61f9b4b55907d79248a37c441
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034900B2

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