Reaktion #1106896

Reaktionsgleichung

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

sodium thiomethoxide

N-methylpyrrolidone

→

title compound

Ausbeute 24.0%

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

Ausbeute 24.0%

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA thick-walled microwave bottle equipped with a stirbar
2. 2
   SonstigeThe bottle was fitted with a septum
3. 3
   Sonstigecap
4. 4
   Waschenwashed with 4×100 volume equivalents of water and 1×100 volume equivalents of brine
5. 5
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo

Vorschrift

A thick-walled microwave bottle equipped with a stirbar was charged with (S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-ol (1.0 equiv), sodium thiomethoxide (4.5 equiv), and N-methylpyrrolidone (10 volume equivalents). The bottle was fitted with a septum and cap and heated to 180° C. in a microwave for 30 min. The reaction mixture was then diluted with 100 volume equivalents of EtOAc and washed with 4×100 volume equivalents of water and 1×100 volume equivalents of brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Reverse-phase preparative HPLC (20%-80% MeCN/H2O) provided the title compound (24%) as a white solid. LCMS m/z (APCI)=287.1 (M+H).

Quelle