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Potassium Carbonate → 2-Butoxy-8-methoxy-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-6-amine

HRID 1010932
ノート
印刷プレビュー

反応式

HRID 1010932 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][CH:33]1[CH2:37][CH2:36][O:35][CH2:34]1>CN(C)C=O>[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][CH:33]2[CH2:37][CH2:36][O:35][CH2:34]2)=[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 141734223-(Bromomethyl)oxolaneHCID 178450370HCID 178450370、化合物

生成物 1

HCID 576996032-Butoxy-8-methoxy-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-6-amine収率 53%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

2-Butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (0.20 g) was dissolved in anhydrous N,N-dimethylformamide (5 mL) was treated with anhydrous potassium carbonate (0.315 g), heated to 60° C. for 1 hour and then cooled to room temperature. To the above was added 3-(bromomethyl)tetrahydrofuran (0.103 g) and the reaction mixture heated at 50° C., overnight. The reaction mixture was quenched with water (25 mL) and extracted into ethyl acetate (3 times, 100 mL combined total volume). The combined organic phase was separated and passed through a hydrophobic frit to dry. The organic phase was stripped to give a gum which was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (20-60%) to afford the title compound as a white solid (97 mg).

後処理

  1. temperaturecooled to room temperature
  2. temperaturethe reaction mixture heated at 50° C., overnight
  3. customThe reaction mixture was quenched with water (25 mL)
  4. extractionextracted into ethyl acetate (3 times, 100 mL combined total volume)
  5. customThe combined organic phase was separated
  6. customto dry
  7. customto give a gum which
  8. customwas purified by C18 reverse phase chromatography

出典と根拠

ORDレコード
ord-d9a3d438a04642ec8fdf822a6e281a42
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07977344B2

反応ノート

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