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

HRID 1097649

반응식

HRID 1097649 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6e191fc6709e4d269f33ab4ef029e30e
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143264B2

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