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Potassium Carbonate → 2-(Butyloxy)-9-(4-chlorobutyl)-8-(methyloxy)-9H-purin-6-amine

HRID 527771
ノート
印刷プレビュー

反応式

HRID 527771 の反応式
FC(F)(F)C(O)=O.[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][CH2:35][Cl:36]>CN(C=O)C>[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:32][CH2:33][CH2:34][CH2:35][Cl:36])=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]
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 178450370HCID 178450370、化合物

生成物 1

HCID 592526152-(Butyloxy)-9-(4-chlorobutyl)-8-(methyloxy)-9H-purin-6-amine収率 75.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

2-(Butyloxy)-8-(methyloxy)-9H-purin-6-amine trifluoroacetate (2 g, 5.69 mmol) and potassium carbonate (1.967 g, 14.23 mmol) were suspended in DMF (20 ml) and heated to 50° C., under nitrogen for 30 mins. The mixture was cooled to room temperature, 1-bromo-4-chlorobutane (0.656 ml, 5.69 mmol) was added and stirring continued at room temperature for 20 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between DCM (40 ml) and water (40 ml). The layers were separated using a hydrophobic frit and the aqueous layer washed with DCM (10 ml). The combined organic extracts were concentrated in vacuo to give crude material that was purified by silica chromatography using the FlashMaster (70 g cartridge) eluting with a cyclohexane:ethyl acetate 0-100% gradient over 30 mins. The product-containing fractions were combined and evaporated to give the title compound as a white solid (1.4 g).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between DCM (40 ml) and water (40 ml)
  4. customThe layers were separated
  5. washthe aqueous layer washed with DCM (10 ml)
  6. concentrationThe combined organic extracts were concentrated in vacuo
  7. customto give crude material that
  8. customwas purified by silica chromatography
  9. washeluting with a cyclohexane
  10. waitethyl acetate 0-100% gradient over 30 mins
  11. customevaporated

出典と根拠

ORDレコード
ord-75bae4e445954411bf67e0c82a299972
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09346806B2

反応ノート

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