反応 #6791

反応方程式

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

4-(methylthio)phenylboronic acid

sodium carbonate

→

title compound

収率 84.0%

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

収率 84.0%

溶媒

DME

water

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度under reflux
3. 3
   濃縮The reaction mixture was concentrated in vacuo
4. 4
   その他the resultant mixture partitioned between ethyl acetate and water
5. 5
   その他The organic phase was separated
6. 6
   洗浄washed with water
7. 7
   乾燥dried (Na2SO4)
8. 8
   濃縮concentrated in vacuo to a purple solid
9. 9
   その他Purification by flash column chromatography with cyclohexane

実験手順

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%).

出典