Reaktion #2288384

Reaktionsgleichung

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 methanesulfonate

potassium thioacetate

→

title compound

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

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated at 70° C. overnight
2. 2
   Temperaturafter cooling to RT
3. 3
   Sonstigethe mixture was partitioned between EtOAc (100 ml) and water (150 ml)
4. 4
   SonstigeThe layers were separated
5. 5
   Extraktionthe aqueous was extracted with EtOAc (×3)
6. 6
   Waschenwashed with water, brine (×3)
7. 7
   Einengenconcentrated in vacuo

Vorschrift

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 methanesulfonate (step 3)(1.3 g, 2.63 mmol) in dry DMF (20 ml) was treated with potassium thioacetate (1.5 g, 13.1 mmol). The resulting solution stirred for 7 h at 70° C. and at RT for 3 days. The mixture was heated at 70° C. overnight and after cooling to RT, the mixture was partitioned between EtOAc (100 ml) and water (150 ml). The layers were separated and the aqueous was extracted with EtOAc (×3). The organics were combined, washed with water, brine (×3), passed through a hydrophobic frit and concentrated in vacuo to yield the title compound as a brown oil;

Quelle