Reaktion #6791

Reaktionsgleichung

4-chloro-2-methylthio-6-(trifluoromethyl)pyrimidine

4-(methylthio)phenylboronic acid

sodium carbonate

→

title compound

Ausbeute 84.0%

2-(Methylthio)-4-[4(methylthio)phenyl]-6-(trifluoromethyl)pyrimidine

Ausbeute 84.0%

Lösungsmittel

DME

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux
3. 3
   EinengenThe reaction mixture was concentrated in vacuo
4. 4
   Sonstigethe resultant mixture partitioned between ethyl acetate and water
5. 5
   SonstigeThe organic phase was separated
6. 6
   Waschenwashed with water
7. 7
   Trocknendried (Na2SO4)
8. 8
   Einengenconcentrated in vacuo to a purple solid
9. 9
   SonstigePurification by flash column chromatography with cyclohexane

Vorschrift

A mixture of 4-chloro-2-methylthio-6-(trifluoromethyl)pyrimidine (ButtPark Ltd, 2.86 g, 14.55 mmol), 4-(methylthio)phenylboronic acid (Aldrich, 2.83 g, 1.1 eq), tetrakistriphenylphosphine palladium (0) (0.2 g) and sodium carbonate (4.04 g, 2.6 eq) in DME (200 ml) and water (100 ml) was heated under reflux with stirring under N2 for 24 h. The reaction mixture was concentrated in vacuo and the resultant mixture partitioned between ethyl acetate and water. The organic phase was separated, washed with water, dried (Na2SO4) and concentrated in vacuo to a purple solid. Purification by flash column chromatography with cyclohexane:ethyl acetate as (6:1) as eluant gave the title compound as a yellow crystalline solid (3.869, 84%).

Quelle