反应详情

温度

80 °C

N-Benzyl-7-bromo-2-chlorothieno[3,2-d]pyrimidin-4-amine (310 mg, 0.874 mmol) was dissolved in acetonitrile (4 mL) and then bis(triphenylphosphine)palladium(II) dichloride (15 mg, 0.022 mmol), CuI (6 mg, 0.350 mmol), dicyclohexylamine (0.19 mL, 0.96 mmol) and ethynyltrimethylsilane (0.24 mL, 1.75 mmol) were added. After flowing nitrogen gas for 15 minutes, the reaction mixture was stirred at 80° C. for 14 hours. After cooling to room temperature, the reaction mixture was filtered with celite and washed with ethyl acetate (50 mL). The filtrate was washed with brine and concentrated by drying with MgSO4. Without purification, the resultant compound was dissolved in anhydrous tetrahydrofuran (5 mL) and then 1.0 M tetrabutylammonium fluoride dissolved in tetrahydrofuran (4.4 mL, 4.4 mmol) was added thereto. The reaction mixture was stirred at room temperature for 30 minutes and then concentrated. Purification of the mixture by silica gel chromatography (ethyl acetate/hexane: 2/8→3/7) yielded the target compound (180 mg, 68% yield).

1. customfor 15 minutes
2. temperatureAfter cooling to room temperature
3. filtrationthe reaction mixture was filtered with celite
4. washwashed with ethyl acetate (50 mL)
5. washThe filtrate was washed with brine
6. concentrationconcentrated
7. dry with materialby drying with MgSO4
8. customWithout purification
9. dissolutionthe resultant compound was dissolved in anhydrous tetrahydrofuran (5 mL)
10. additionwas added
11. stirringThe reaction mixture was stirred at room temperature for 30 minutes
12. concentrationconcentrated
13. customPurification of the mixture by silica gel chromatography (ethyl acetate/hexane: 2/8→3/7)