Water → HCID 86711275, Verbindung

HRID 336135Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336135
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:9]2[C:16]([I:17])=[CH:15][NH:14][C:10]=2[N:11]=[CH:12][N:13]=1.Br[CH2:19][CH:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH:21]=[CH2:22].O>CN(C=O)C.C(OCC)(=O)C>[Si:24]([O:23][CH:20]([CH:21]=[CH2:22])[CH2:19][N:14]1[C:10]2[N:11]=[CH:12][N:13]=[C:8]([Cl:7])[C:9]=2[C:16]([I:17])=[CH:15]1)([C:27]([CH3:28])([CH3:29])[CH3:30])([CH3:25])[CH3:26]

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 148092816-Chloro-7-iodo-7-deazapurineHCID 86711274HCID 86711274, Verbindung

Produkt 1

HCID 86711275HCID 86711275, VerbindungAusbeute 36,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Potassium carbonate (2.2 g) was added to a solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (3.7 g) obtained in Step 1 and 1-bromo-2-(tert-butyldimethylsilyloxy)-3-butene (3.5 g) obtained in Step 2 in DMF (26 ml) at room temperature, and the mixture was stirred at 80° C. for 5 hours. After cooling the reaction mixture, water and ethyl acetate were added thereto, and the generated insoluble matter was filtered off. The organic layer was separated, washed with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a light-yellow solid (2.25 g).

Aufarbeitung

  1. additionwere added
  2. filtrationthe generated insoluble matter was filtered off
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-b7b70a835f8947f3aa6f5004b06c7970
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889666B2

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