反应详情

温度

-78 °C

Thienyl lithium (1.0 M in THF, 26 mL, 26 mmol) was diluted with anhydrous THF (65 mL) and the mixture cooled down to −78° C. under a nitrogen atmosphere. 5-Bromo-2-chloropyrimidine, dissolved in 10 mL of tetrahydofuran, was added to the reaction mixture dropwise. The reaction was allowed to stir for 1 h and then warmed to −20° C. Acetic acid (1.5 mL) and methanol (1.2 mL) were successively added to the reaction mixture. The reaction was stirred for 15 min and a solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (5.9 g, 20 mmol) in 10 mL of THF was added. The reaction was stirred for an additional 15 min and then the cooling bath was removed. The mixture was stirred for 1 h and then cooled to 0° C. with an ice bath. 5 N sodium hydroxide (5.2 mL) was added to the reaction mixture and stirred for 5 min. The reaction was then diluted with ethyl acetate (50 mL) and water (50 mL). The organic layer was washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was then dried with sodium sulfate, concentrated and purified by flash chromatography on silica gel using 5% ethyl acetate in hexanes as an eluent to obtain a yellow solid. Yield=3.6 g. MS (M+H)+ 275/277.

1. additionwas added to the reaction mixture dropwise
2. temperaturewarmed to −20° C
3. stirringThe reaction was stirred for 15 min
4. stirringThe reaction was stirred for an additional 15 min
5. customthe cooling bath was removed
6. stirringThe mixture was stirred for 1 h
7. temperaturecooled to 0° C. with an ice bath
8. addition5 N sodium hydroxide (5.2 mL) was added to the reaction mixture
9. stirringstirred for 5 min
10. additionThe reaction was then diluted with ethyl acetate (50 mL) and water (50 mL)
11. washThe organic layer was washed with saturated aqueous sodium bicarbonate, water and brine
12. dry with materialThe organic layer was then dried with sodium sulfate
13. concentrationconcentrated
14. custompurified by flash chromatography on silica gel using 5% ethyl acetate in hexanes as an eluent
15. customto obtain a yellow solid