N-bromobutanimide → 8-Bromo-2-{[2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 1011024ノート

反応式

HRID 1011024 の反応式
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[CH:11][N:12]2[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[C:8]([NH2:21])[N:7]=1.[Br:22]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:22][C:11]1[N:12]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[C:13]2[C:9]([N:10]=1)=[C:8]([NH2:21])[N:7]=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[N:14]=2

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 57699621[2-(Methoxy)ethyl]oxy-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

生成物 1

HCID 576997398-Bromo-2-{[2-(methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine収率 70.9%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

2-{[2-(Methoxy)ethyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.61 g) was dissolved in chloroform (20 mL) and cooled to 0° C. To this solution was then added N-bromosuccinimide (1.02 g) gradually, keeping the temperature at ˜2° C. The reaction was stirred at 2° C. for around 15 minutes before being allowed to warm to room temperature. The reaction mixture was then stirred under nitrogen for 5 hours. The reaction mixture was quenched with water (100 mL) and stirred rapidly before the organic layer was separated using a hydrophobic frit. The organic was evaporated under reduced pressure to give a dark brown gum. This material was purified by silica chromatography (ISCO) eluting initially with 0-70% ethyl acetate: cyclohexane holding isocratic at 70% ethyl acetate; cyclohexane until a minor impurity was eluted. The gradient was then resumed from 70%-95% ethyl acetate: cyclohexane. This gave the title compound as a white solid (1.4489 g)

後処理

  1. customat ˜2° C
  2. temperatureto warm to room temperature
  3. stirringThe reaction mixture was then stirred under nitrogen for 5 hours
  4. customThe reaction mixture was quenched with water (100 mL)
  5. stirringstirred rapidly before the organic layer
  6. customwas separated
  7. customThe organic was evaporated under reduced pressure
  8. customto give a dark brown gum
  9. customThis material was purified by silica chromatography (ISCO)
  10. washeluting initially with 0-70% ethyl acetate
  11. washcyclohexane until a minor impurity was eluted

出典と根拠

ORDレコード
ord-8614b8e95dbb4d0894a89e294f1ca779
出典データセット
uspto-grants-2011_07
特許番号
US07977344B2

反応ノート

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