Reaktion #2507862

Reaktionsgleichung

triethylamine

tributyl(1-ethoxyvinyl)stannane

(S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol

→

title compound

Ausbeute 33.0%

(S)-1-(2-hydroxy-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-6-yl)ethanone

Ausbeute 33.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAn oven-dried scintillation vial equipped with a stirbar
2. 2
   Sonstigepurged with nitrogen for 5 min
3. 3
   SonstigeThe reaction was quenched with 1 N KHSO4
4. 4
   workup.ADDITIONThe mixture was then diluted with EtOAc
5. 5
   Waschenwashed twice with NaHCO3 and once with brine
6. 6
   TrocknenThe organic layer was dried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated in vacuo

Vorschrift

An oven-dried scintillation vial equipped with a stirbar was charged with (S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol (1.0 equiv), and (Ph3P)4Pd (0.07 equiv). The bottle was covered with a sheet of Parafilm and purged with nitrogen for 5 min, and anhydrous dioxane (13 volume equivalents), triethylamine (3.0 equiv), and tributyl(1-ethoxyvinyl)stannane (1.5 equiv) were added by syringe. The resulting mixture was heated to 80° C. overnight. The reaction was quenched with 1 N KHSO4 and stirred for 30 min. The mixture was then diluted with EtOAc, washed twice with NaHCO3 and once with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Biotage MPLC 10%-66% EtOAc/Hexanes) provided the title compound (33%) as a white solid. LCMS m/z (APCI)=283.1 (M+H).

Quelle