Reaktion #2507872

Reaktionsgleichung

6-bromo-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyrazin-2-ol

trimethylsilylacetylene

triethylamine

→

title compound

Ausbeute 80.2%

1-(pentan-3-yl)-6-((trimethylsilyl)ethynyl)-1H-imidazo[4,5-b]pyrazin-2-ol

Ausbeute 80.2%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas purged with N2 for 30 seconds
2. 2
   workup.ADDITIONAfter 3 hours the reaction mixture was diluted with EtOAc
3. 3
   Waschenwashed with NH4Cl solution
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigePurification with over silica gel (Biotage MPLC 10-80% EtOAc/hexanes)

Vorschrift

A mixture of 6-bromo-1-(pentan-3-yl)-1H-imidazo[4,5-b]pyrazin-2-ol (3.75 g, 13.2 mmol)), trimethylsilylacetylene (2.8 mL, 19.8 mmol), PdCl2(PPh)2 (0.93 g, 1.32 mmol), CuI (0.5 g, 2.64 mmol) and triethylamine (5.5 mL, 39.5 mmol) in DMF (50 mL) was purged with N2 for 30 seconds followed by stirring at 80° C. After 3 hours the reaction mixture was diluted with EtOAc, washed with NH4Cl solution, dried over Na2SO4, and concentrated in vacuo. Purification with over silica gel (Biotage MPLC 10-80% EtOAc/hexanes) provided the title compound (3.2 g, 80%) as a brown solid.

Quelle