Cesium carbonate → 8-chloro-1-(3-hydroxypropyl)-7-(2-propen-1-yl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1097649

反応式

HRID 1097649 の反応式
[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH3:18])[C:4]=2[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][CH2:27][CH2:28][OH:29]>CN(C=O)C>[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[N:7]([CH2:26][CH2:27][CH2:28][OH:29])[C:6](=[O:15])[N:5]([CH2:16][CH2:17][CH3:18])[C:4]=2[N:3]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 123083-Bromo-1-propanolHCID 592995678-chloro-7-(2-propen-1-yl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione

生成物 1

HCID 593956018-chloro-1-(3-hydroxypropyl)-7-(2-propen-1-yl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione収率 71.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A solution of 8-chloro-7-(2-propen-1-yl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione (3.0 g, 11.1 mmol) in DMF (20 ml) was treated with caesium carbonate (3.7 g, 11.4 mmol) and 3-bromo-1-propanol (1.6 g, 11.5 mmol). The mixture was heated at 60° C. for 4 h and then cooled and evaporated. The residue was partitioned between EtOAc (60 ml) and saturated aqueous sodium bicarbonate (50 ml). The aqueous phase was extracted with EtOAc (60 ml), the combined organic phases were dried (MgSO4), filtered and evaporated. The product was purified using the Companion™ system and a gradient elution from cyclohexane to EtOAc. Product containing fractions were combined and evaporated to give the title compound as a colourless oil (2.6 g).

後処理

  1. temperaturecooled
  2. customevaporated
  3. customThe residue was partitioned between EtOAc (60 ml) and saturated aqueous sodium bicarbonate (50 ml)
  4. extractionThe aqueous phase was extracted with EtOAc (60 ml)
  5. dry with materialthe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe product was purified
  9. washa gradient elution from cyclohexane to EtOAc
  10. additionProduct containing fractions
  11. customevaporated

出典と根拠

ORDレコード
ord-6e191fc6709e4d269f33ab4ef029e30e
出典データセット
uspto-grants-2012_03
特許番号
US08143264B2

関連ノート

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