(2S)-hexan-2-ol → 2-{[(1S)-1-Methylpentyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 527801ノート

反応式

HRID 527801 の反応式
CC(C)([O-])C.[Na+].[CH3:7][C@H:8]([OH:13])[CH2:9][CH2:10][CH2:11][CH3:12].F[C:15]1[N:23]=[C:22]2[C:18]([N:19]=[CH:20][N:21]2[CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)=[C:17]([NH2:30])[N:16]=1>COCCOC>[CH3:7][C@H:8]([O:13][C:15]1[N:23]=[C:22]2[C:18]([N:19]=[CH:20][N:21]2[CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)=[C:17]([NH2:30])[N:16]=1)[CH2:9][CH2:10][CH2:11][CH3:12]

参加物

5

反応物 3

HCID 638097(2S)-hexan-2-olHCID 23676156Sodium t-butoxideHCID 592525662-Fluoro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

生成物 1

HCID 592526582-{[(1S)-1-Methylpentyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine収率 41.2%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

Sodium t-butoxide (4.86 g, 50.6 mmol) was added portionwise to a stirred mixture of (S)-2-hexanol (12 g, 117 mmol) and 1,2-dimethoxyethane (12 ml). The resultant mixture was heated to 50° C. under an atmosphere of nitrogen and then 2-fluoro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (3 g, 12.65 mmol) was added. The resultant mixture was maintained at 50° C. for 20 hours when LCMS indicated complete reaction. The mixture was cooled to room temperature and partitioned between ethyl acetate (100 ml) and water (100 ml). The organic phase was washed with water (100 ml) then saturated brine (50 ml), dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was dissolved in dichloromethane and purified on an aminopropyl (NH2) cartridge (100 g) eluting with a 0-100% ethyl acetate in cyclohexane gradient over 40 mins. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a white foam (1.665 g).

後処理

  1. customreaction
  2. custompartitioned between ethyl acetate (100 ml) and water (100 ml)
  3. washThe organic phase was washed with water (100 ml)
  4. dry with materialsaturated brine (50 ml), dried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe residue was dissolved in dichloromethane
  8. custompurified on an aminopropyl (NH2) cartridge (100 g)
  9. washeluting with a 0-100% ethyl acetate in cyclohexane gradient over 40 mins
  10. customevaporated in vacuo

出典と根拠

ORDレコード
ord-c1734fc37cbc4d8f9175000feb967e87
出典データセット
uspto-grants-2016_05
特許番号
US09346806B2

反応ノート

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