反应详情

温度

-50 °C

TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) was added to a solution of 1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione (12) (194 mg, 1.0 mmol) in THF (2 mL) at 25° C. and the reaction mixture was then stirred at this temperature for max. 5 min. After cooling down to −50 ° C., ethyl 2-(bromomethyl)acrylate (230 mg, 1.2 mmol) and CuCN.2LiCl (1.0 M solution in THF, 5 drops) were added and the resulting mixture was allowed to warm up slowly overnight. The reaction mixture was quenched with a sat. aq. NH4Cl solution (20 mL), extracted with diethyl ether (3×50 mL) and dried over anhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/ether, 1:1) furnished compound 14b (211 mg, 69%) as a colourless solid.

1. custom5 min
2. temperatureto warm up slowly overnight
3. customThe reaction mixture was quenched with a sat. aq. NH4Cl solution (20 mL)
4. extractionextracted with diethyl ether (3×50 mL)
5. dry with materialdried over anhydrous Na2SO4
6. filtrationAfter filtration
7. customthe solvent was evaporated in vacuo
8. customPurification by flash-chromatography (CH2Cl2/ether, 1:1)