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

HRID 1097649

Reaktionsgleichung

Reaktionsgleichung von HRID 1097649
[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

Komponenten

5

Edukt 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

Produkt 1

HCID 593956018-chloro-1-(3-hydroxypropyl)-7-(2-propen-1-yl)-3-propyl-3,7-dihydro-1H-purine-2,6-dioneAusbeute 71,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6e191fc6709e4d269f33ab4ef029e30e
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143264B2

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