反应 #2507861

反应方程式

CDI

(S)-6-bromo-N2-(1-phenylethyl)pyrazine-2,3-diamine

carbonyldiimidazole

→

title compound

收率 66.0%

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

收率 66.0%

溶剂

THF

反应条件

后处理

1. 1
   其他was consumed (approx. 3.6 equiv total)
2. 2
   其他After complete reaction
3. 3
   其他quenched by the careful addition of water until gas evolution
4. 4
   workup.ADDITIONThe mixture was diluted with 25 volume equivalents of EtOAc
5. 5
   洗涤washed with 3×7.5 volume equivalents of water and 1×7.5 volume equivalents of brine
6. 6
   干燥The organic layer was dried over anhydrous sodium sulfate
7. 7
   过滤filtered
8. 8
   浓缩concentrated in vacuo

实验过程

To a solution of (S)-6-bromo-N2-(1-phenylethyl)pyrazine-2,3-diamine (1.0 equiv) in refluxing anhydrous THF (5 volume equivalents) was added carbonyldiimidazole (CDI). Successive portions of CDI were added until the starting material was consumed (approx. 3.6 equiv total) as judged by TLC (50% EtOAc/Hexanes). After complete reaction, the mixture was cooled to room temperature and quenched by the careful addition of water until gas evolution had ceased. The mixture was diluted with 25 volume equivalents of EtOAc and washed with 3×7.5 volume equivalents of water and 1×7.5 volume equivalents of brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Flash chromatography (Biotage MPLC 5%-40% EtOAc/Hexanes) provided the title compound (66%) as a white solid. LCMS m/z (APCI)=319.0, 321.0 (M+H).

来源