Reaktion #2288353

Reaktionsgleichung

6-(2-mercapto-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione

Intermediate A

6-(2-mercapto-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione

bismuth triflate

5-methylfuran-2-carbaldehyde

→

title compound

1,3-Dimethyl-10-(5-methylfuran-2-yl)-5-phenyl-7,8-dihydro-1H-pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,4]thiazine-2,4(3H,10H)-dione

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to RT
2. 2
   Sonstigethe solvent was removed under reduced pressure
3. 3
   SonstigeThe residue was partitioned between EtOAc (20 mL) and water (20 mL)
4. 4
   Sonstigethe phases separated
5. 5
   ExtraktionThe aqueous phase was extracted with EtOAc (2×20 ml) the combined organic phases
6. 6
   Trocknenwere dried over magnesium sulfate
7. 7
   Sonstigethe solvent removed under vacuum
8. 8
   SonstigePurification by chromatography on silica
9. 9
   Wascheneluting with 0-50% EtOAc/hexane

Vorschrift

To 6-(2-mercapto-ethyl)-1,3-dimethyl-5-phenyl-1,6-dihydro-pyrrolo[3,4-d]pyrimidine-2,4-dione (Intermediate A) (207 mg, 0.656 mmol) and bismuth triflate (43.1 mg, 0.066 mmol) in toluene (5 ml) was added 5-methylfuran-2-carbaldehyde (commercial) (0.065 ml, 0.656 mmol) the mixture heated to 100° C. for 1 hour. The reaction mixture was cooled to RT and the solvent was removed under reduced pressure. The residue was partitioned between EtOAc (20 mL) and water (20 mL) and the phases separated. The aqueous phase was extracted with EtOAc (2×20 ml) the combined organic phases were dried over magnesium sulfate and the solvent removed under vacuum. Purification by chromatography on silica, eluting with 0-50% EtOAc/hexane gave the title compound.

Quelle