Sodium Carbonate → 8-chloro-7-(2-propen-1-yl)-3-(4,4,4-trifluorobutyl)-3,7-dihydro-1H-purine-2,6-dione

HRID 2386605

Reaktionsgleichung

Reaktionsgleichung von HRID 2386605
[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])[NH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:23][CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27]>CN(C)C=O>[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]([CH2:23][CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27])[C:4]=2[N:3]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 592995327-Allyl-8-chloro-1H-purine-2,6(3H,7H)-dione

Produkt 1

HCID 592995888-chloro-7-(2-propen-1-yl)-3-(4,4,4-trifluorobutyl)-3,7-dihydro-1H-purine-2,6-dioneAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (1.5 g, 6.64 mmol), sodium carbonate (844 mg, 7.9 mmol) and 4-bromo-1,1,1-trifluorobutane (1.39 g, 7.3 mmol) were stirred in dimethylformamide (25 ml, dry) for seven days. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was separated and washed with hydrochloric acid (2N), brine, dried (MgSO4) and then evaporated to dryness. The crude product was triturated with ether and the solid collected by filtration to afford 8-chloro-7-(2-propen-1-yl)-3-(4,4,4-trifluorobutyl)-3,7-dihydro-1H-purine-2,6-dione as a white solid (1.23 g, 57%). m/z 337 [MH+].

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic phase was separated
  3. washwashed with hydrochloric acid (2N), brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe crude product was triturated with ether
  7. filtrationthe solid collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-0b4b9ed5926243d4b27b7c71597e5555
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268839B2

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