Reaktion #2288385

Reaktionsgleichung

TFA

S-(1-((tert-butyldimethylsilyl)oxy)-3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl) ethanethioate

S-(1-((tert-Butyldimethylsilyl)oxy)-3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl) ethanethioate

sodium borohydride

→

title compound

6-(3-Hydroxy-2-mercaptopropyl)-1,3-dimethyl-5-phenyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Lösungsmittel

water

DCM

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting solid was removed by filtration
2. 2
   Einengenthe filtrate was concentrated in vacuo
3. 3
   Sonstigeto remove EtOH
4. 4
   workup.ADDITIONThe resulting mixture was diluted with water
5. 5
   Extraktionextracted with DCM (×3)
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   Sonstigeto afford an oil
8. 8
   Sonstigepurified via ISCO column chromatography, 12 g, liquid load, 0-90% EtOAc in iso-hexane

Vorschrift

To a stirred solution of S-(1-((tert-butyldimethylsilyl)oxy)-3-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)propan-2-yl) ethanethioate (step 4) (1.62 g, 3.23 mmol) in EtOH (25 ml) was added sodium borohydride (0.61 g, 16.14 mmol) at 0° C. and the solution stirred overnight at RT. The reaction mixture was added slowly to TFA in water (20 ml, 50%). The resulting solid was removed by filtration and the filtrate was concentrated in vacuo to remove EtOH. The resulting mixture was diluted with water and extracted with DCM (×3). The combined organic extracts were passed through a hydrophobic frit and concentrated under reduced pressure to afford an oil. The oil was dissolved in a minimal volume of DCM and purified via ISCO column chromatography, 12 g, liquid load, 0-90% EtOAc in iso-hexane to afford the title compound;

Quelle