Reaktion #1596090

Reaktionsgleichung

2-(3-chlorophenyl)-6-(trifluoromethyl)pyrimidin-4(3H)-one

POCl3

→

title compound

Ausbeute 87.5%

4-chloro-2-(3-chlorophenyl)-6-(trifluoromethyl)pyrimidine

Ausbeute 87.5%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Einengenthe mixture was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in dichloromethane (50 mL)
4. 4
   workup.ADDITIONtreated with aqueous sodium, bicarbonate until the pH˜8
5. 5
   ExtraktionThe aqueous layer was extracted with dichloromethane (4×25 mL)
6. 6
   ExtraktionThe combined organic extract
7. 7
   Waschenwas washed the saturated sodium chloride (20 mL)
8. 8
   Trocknendried over sodium sulfate
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated under reduced pressure
11. 11
    SonstigeThe residue was purified by silica chromatography

Vorschrift

A 250-mL round bottom flask was charged with 2-(3-chlorophenyl)-6-(trifluoromethyl)pyrimidin-4(3H)-one (3.60 g, 13.1 mmol). POCl3 (14.4 mL, 157 mmol) was cautiously added at 0° C. The resulting mixture was stirred at 100° C. for 3.5 h. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane (50 mL) and treated with aqueous sodium, bicarbonate until the pH˜8. The aqueous layer was extracted with dichloromethane (4×25 mL). The combined organic extract was washed the saturated sodium chloride (20 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica chromatography using hexanes/dichloromethane (3:1) as eluent to afford the title compound (3.36 g, 87%) as a white solid. MW=293.07. 1H NMR (CDCl3, 500 MHz) δ 8.49 (t, J=1.5 Hz, 1H), 8.39 (dt, J=8.0, 1.5 Hz, 1H), 7.57 (s, 1H), 7.53 (ddd, J=8.0, 2.0, 1.0 Hz, 1H), 7.45 (t, J=8.0 Hz, 1H).

Quelle