Reaktion #2288392

Reaktionsgleichung

Trifluoroacetic acid

bismuth triflate

5-chlorofuran-2-carbaldehyde

6-(3-((tert-butyldimethylsilyl)oxy)-2-mercaptopropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

→

title compound

10-(5-Chlorofuran-2-yl)-5-(3-fluorophenyl)-8-(hydroxymethyl)-1,3-dimethyl-7,8-dihydro-1H-pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,4]thiazine-2,4(3H,10H)-dione

Lösungsmittel

DCM

NaOH

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe phases were separated
2. 2
   Extraktionthe aqueous phase was extracted with DCM (3×10 mL)
3. 3
   TrocknenThe combined organic extracts were dried over magnesium sulfate
4. 4
   Sonstigeevaporated under vacuum
5. 5
   SonstigePurification by chromatography on silica
6. 6
   Wascheneluting with 0-50% EtOAc/hexane

Vorschrift

Trifluoroacetic acid (161 μl, 2.094 mmol) was added to a solution of bismuth triflate (41.2 mg, 0.063 mmol), 5-chlorofuran-2-carbaldehyde (30.1 mg, 0.230 mmol) and 6-(3-((tert-butyldimethylsilyl)oxy)-2-mercaptopropyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (100 mg, 0.209 mmol) in toluene (2094 μL). The mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with DCM (10 mL) and 1M NaOH(aq) (10 mL). The phases were separated and the aqueous phase was extracted with DCM (3×10 mL). The combined organic extracts were dried over magnesium sulfate and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-50% EtOAc/hexane, afforded the title compound as a mixture of diastereomers.

Quelle