反应详情

温度

50 °C

A mixture of ethyl 1-(benzyloxymethyl)-4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohex-3-enecarboxylate (3.06 g, 4.59 mmol) and Pd/C (cat.) in THF (25 mL) was heated at 50° C. under 1.0 atm of H2 for 16 h. LCMS indicated complete reduction of double bond. The reaction mixture was filtered and evaporated. The residue was dissolved in MeOH and HCO2NH4 and Pd/C (cat.) was added. The resulting mixture was heated under reflux for 24 h. After cooling to rt, the reaction mixture was filtered. The filtrate was concentrated and purified by a SiO2 column (0-40% EtOAc/Hexanes, Rf=0.5 in 50% EtOAc) to afford ethyl 4-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-1-(hydroxymethyl)cyclohexanecarboxylate as colorless oil (733 mg). HPLC-MS TR=2.78 min (UV 254 nm, 5 min method); mass calculated for formula C28H50N4O5Si2 578.3, observed LCMS m/z 579.2 (M+H).

1. filtrationThe reaction mixture was filtered
2. customevaporated
3. dissolutionThe residue was dissolved in MeOH
4. additionHCO2NH4 and Pd/C (cat.) was added
5. temperatureThe resulting mixture was heated
6. temperatureunder reflux for 24 h
7. temperatureAfter cooling to rt
8. filtrationthe reaction mixture was filtered
9. concentrationThe filtrate was concentrated
10. custompurified by a SiO2 column (0-40% EtOAc/Hexanes, Rf=0.5 in 50% EtOAc)