反应详情

温度

120 °C

To a solution of (5-Bromo-2-chloro-pyrimidin-4-yl)cyclopentylamine (1 g, 3.616 mmol) is added lithium chloride (153.7 mg, 3.616 mmol) and potassium acetate (887.12 mg, 9.03 mmol) in DMF (50 mL). The solution is degassed and back-filled with N2. Palladium(II) acetate (40.6 mg, 0.18 mmol) is added and the solution is degassed and back-filled with nitrogen three times. 3-pentyn-2-ol (1.0 mL, 10.8 mmol) is added and the reaction solution is heated at 120° C. for 5 hours. LC-MS analysis indicated the absence of starting material and the formation of a pair of regio-isomeric products. After cooling to room temperature, the mixture is filtered through Celite, diluted with water, and extracted with ethyl acetate EtOAc three times. The organic layers are combined, washed with brine and dried over anhydrous sodium sulfate. The solvent is evaporated and the crude material is purified using silica gel chromatography (30% ethyl acetate/70% hexanes to give 1-(2-Chloro-7-cyclopentyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-ethanol as a pale powder (150 mg, 14.8%). [M+H]+=280.07.

1. customThe solution is degassed
2. additionback-filled with N2
3. customthe solution is degassed
4. additionback-filled with nitrogen three times
5. temperatureAfter cooling to room temperature
6. filtrationthe mixture is filtered through Celite
7. additiondiluted with water
8. extractionextracted with ethyl acetate EtOAc three times
9. washwashed with brine
10. dry with materialdried over anhydrous sodium sulfate
11. customThe solvent is evaporated
12. customthe crude material is purified