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Potassium Carbonate → 9-(4-Chlorobutyl)-2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amine

HRID 2036357
ノート
印刷プレビュー

反応式

HRID 2036357 の反応式
[CH3:1][C@H:2]([O:6][C:7]1[NH:8][C:9]([NH2:18])=[C:10]2[C:14]([N:15]=1)=[N:13][C:12]([O:16][CH3:17])=[N:11]2)[CH2:3][CH2:4][CH3:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][CH2:28][CH2:29][Cl:30]>CN(C=O)C>[Cl:30][CH2:29][CH2:28][CH2:27][CH2:26][N:13]1[C:12]([O:16][CH3:17])=[N:11][C:10]2[C:14]1=[N:15][C:7]([O:6][C@@H:2]([CH3:1])[CH2:3][CH2:4][CH3:5])=[N:8][C:9]=2[NH2:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 178448283HCID 178448283、化合物

生成物 1

HCID 582909339-(4-Chlorobutyl)-2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9H-purin-6-amine収率 71.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-1H-purin-6-amine (1 g, 2.74 mmol) and potassium carbonate (0.946 g, 6.84 mmol) in DMF (12.5 ml) were stirred under nitrogen and heated to 50° C. for 1 hour. The mixture was then allowed to cool to ambient temperature and 1-bromo-4-chlorobutane (0.315 ml, 2.74 mmol) was added and stirring was continued under nitrogen at ambient temperature overnight. The mixture was then partitioned between ethyl acetate and water. The aqueous layer was washed with ethyl acetate and the combined organic extracts were washed with saturated brine and passed through a hydrophobic frit and evaporated in vacuo. The residue (1.0322 g) was dissolved in dichloromethane and loaded onto an amino cartridge (70 g) and eluted using a 0-100% ethyl acetate in cyclohexane gradient over 40 minutes. Product fractions were combined and evaporated to give the title compound as an off-white solid (667 mg).

後処理

  1. temperatureto cool to ambient temperature
  2. customThe mixture was then partitioned between ethyl acetate and water
  3. washThe aqueous layer was washed with ethyl acetate
  4. washthe combined organic extracts were washed with saturated brine
  5. customevaporated in vacuo
  6. dissolutionThe residue (1.0322 g) was dissolved in dichloromethane
  7. washeluted
  8. customover 40 minutes
  9. customevaporated

出典と根拠

ORDレコード
ord-038372330ded4009be6cd474d7dadba2
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08575181B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート