反应详情

温度

100 °C

To a solution of methyl 3-(5-(bromomethyl)-6-(4-chlorophenyl)-1-methyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (30 mg, 0.064 mmol) in toluene (2 mL) was added (4-chlorophenyl)boronic acid (9.94 mg, 0.064 mmol) and aq. Cs2CO3 solution (1 M, 0.5 mL). The reaction was degassed under nitrogen gas (3×) then Pd(PPh3)4 (3 mg) was added. The reaction was heated at 100° C. for 18 h, cooled to RT then diluted with EA (10 mL). The organic layer was washed with brine (5 mL), dried over Na2SO4 and concentrated to a residue which was purified by Prep TLC eluted with PE/EA (1:1) to give methyl 3-(5-(4-chlorobenzyl)-6-(4-chlorophenyl)-1-methyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propanoate (13 mg, 40.6% yield) as a white solid. LCMS: MH+ 503 and TR=2.145 min.

1. customThe reaction was degassed under nitrogen gas (3×)
2. additionPd(PPh3)4 (3 mg) was added
3. temperaturecooled to RT
4. additionthen diluted with EA (10 mL)
5. washThe organic layer was washed with brine (5 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated to a residue which
8. customwas purified by Prep TLC
9. washeluted with PE/EA (1:1)