反应详情

2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-amine (125 mg, 0.2237 mmol) dissolved in PhMe (3 mL) under N2. AlMe3 in heptane (671.1 μL of 1.0 M, 0.6711 mmol) added at RT and the mixture stirred for 30 mins. A solution of 3-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-3H-isobenzofuran-1-one (130.8 mg, 0.4474 mmol) in DCM (3 mL) added with cooling on an ice bath and the mixture stirred overnight. Reaction mixture re-cooled and water added slowly followed by DCM. After stirring for 30 mins, mixture passed through a phase separator cartridge and filtrate concentrated. Residue taken up in THF (5 mL) and PPh3 (88.02 mg, 0.3356 mmol) then DEAD (42.26 μL, 0.2684 mmol) added at RT under N2. Reaction mixture stirred overnight, then concentrated without heating. Residue partitioned between DCM and brine. Aqueous phase extracted with DCM and combined organics dried and concentrated. Residue taken up in DCM and purified by chromatography (silica, 0-100% EtOAc-petrol gradient elution) to give the title compound as a yellow foam (123 mg, 66% over 2 steps); MS (ES+) 833.3.

1. temperaturewith cooling on an ice bath
2. stirringthe mixture stirred overnight
3. customReaction mixture
4. temperaturere-cooled
5. stirringAfter stirring for 30 mins
6. concentrationconcentrated
7. customReaction mixture
8. stirringstirred overnight
9. concentrationconcentrated
10. temperaturewithout heating
11. customResidue partitioned between DCM and brine
12. extractionAqueous phase extracted with DCM
13. customcombined organics dried
14. concentrationconcentrated
15. custompurified by chromatography (silica, 0-100% EtOAc-petrol gradient elution)