反応 #67082

反応方程式

chloro(3-chlorobenzyl)zinc tetrahydrofuran

4-{[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}thiomorpholine 1,1-dioxide

tetrahydrofuran

→

4-{[2-(3-chlorobenzyl)-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}thiomorpholine 1,1-dioxide

溶媒

water

反応条件

後処理

1. 1
   抽出the aqueous layer was extracted with ethyl acetate
2. 2
   洗浄The organic layer was washed with water and saturated brine
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated
6. 6
   その他The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)
7. 7
   workup.ADDITIONTo the obtained pale yellow solid were added 1,4-dioxane (10 mL) and 1-methylpiperazine (0.16 mL)
8. 8
   workup.STIRRINGby stirring at room temperature for 6 hours
9. 9
   workup.ADDITIONTo the reaction mixture was added water
10. 10
    抽出the aqueous layer was extracted with ethyl acetate
11. 11
    洗浄The organic layer was washed with water and saturated brine
12. 12
    乾燥dried over anhydrous magnesium sulfate
13. 13
    ろ過filtered
14. 14
    濃縮concentrated
15. 15
    その他The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate)
16. 16
    洗浄The obtained white solid was washed with ethanol

実験手順

To a mixture of 4-{[2-chloro-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}thiomorpholine 1,1-dioxide (500 mg), dichlorobis(triphenylphosphine)nickel (II) (190 mg), tetrahydrofuran (10 mL) was added a 0.5 M chloro(3-chlorobenzyl)zinc tetrahydrofuran solution (3.2 mL), followed by stirring at room temperature for 6 hours. To the reaction mixture was added water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, then dried over anhydrous magnesium sulfate, filtered, and concentrated. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate). To the obtained pale yellow solid were added 1,4-dioxane (10 mL) and 1-methylpiperazine (0.16 mL), followed by stirring at room temperature for 6 hours. To the reaction mixture was added water and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, then dried over anhydrous magnesium sulfate, filtered, and concentrated. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate). The obtained white solid was washed with ethanol to obtain 4-{[2-(3-chlorobenzyl)-4-(trifluoromethyl)pyrimidin-5-yl]carbonyl}thiomorpholine 1,1-dioxide (212 mg) as a white solid.

出典