N-bromobutanimide → 8-Bromo-2-[(tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-Pyran-2-yl)-9H-purin-6-amine
反応式
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][O:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)=[C:10]([NH2:23])[N:9]=1.[Br:24]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:24][C:13]1[N:14]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[C:15]2[C:11]([N:12]=1)=[C:10]([NH2:23])[N:9]=[C:8]([O:7][CH2:6][CH:2]1[CH2:3][CH2:4][CH2:5][O:1]1)[N:16]=2参加物
4
反応条件
- 温度
- 1 °C
実験手順
2-[(Tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.7202 g) was dissolved in chloroform (15 mL) and cooled to ˜1° C. before N-bromosuccinimide (1.056 g) was added keeping the reaction temperature below 2° C. The reaction mixture was then stirred at ˜1° C. for 30 minutes before allowing to warm to room temperature were upon the reaction mixture was stirred for 3 hours. The reaction mixture was then stood overnight at room temperature before being partitioned between water (50 mL) and the organic phase separated using a hydrophobic frit. The organic phase was evaporated under reduced pressure to give a brown gum which was purified using silica chromatography (ISCO) eluting with 0-100% ethyl acetate: cyclohexane. This gave the title compound as a white foam solid (1.3748 g).