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Potassium Carbonate → 2-(Butyloxy)-9-(4-chlorobutyl)-8-(methyloxy)-9H-purin-6-amine

HRID 527771
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 527771
FC(F)(F)C(O)=O.[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][CH2:35][Cl:36]>CN(C=O)C>[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:32][CH2:33][CH2:34][CH2:35][Cl:36])=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 178450370HCID 178450370, Verbindung

Produkt 1

HCID 592526152-(Butyloxy)-9-(4-chlorobutyl)-8-(methyloxy)-9H-purin-6-amineAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

2-(Butyloxy)-8-(methyloxy)-9H-purin-6-amine trifluoroacetate (2 g, 5.69 mmol) and potassium carbonate (1.967 g, 14.23 mmol) were suspended in DMF (20 ml) and heated to 50° C., under nitrogen for 30 mins. The mixture was cooled to room temperature, 1-bromo-4-chlorobutane (0.656 ml, 5.69 mmol) was added and stirring continued at room temperature for 20 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between DCM (40 ml) and water (40 ml). The layers were separated using a hydrophobic frit and the aqueous layer washed with DCM (10 ml). The combined organic extracts were concentrated in vacuo to give crude material that was purified by silica chromatography using the FlashMaster (70 g cartridge) eluting with a cyclohexane:ethyl acetate 0-100% gradient over 30 mins. The product-containing fractions were combined and evaporated to give the title compound as a white solid (1.4 g).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between DCM (40 ml) and water (40 ml)
  4. customThe layers were separated
  5. washthe aqueous layer washed with DCM (10 ml)
  6. concentrationThe combined organic extracts were concentrated in vacuo
  7. customto give crude material that
  8. customwas purified by silica chromatography
  9. washeluting with a cyclohexane
  10. waitethyl acetate 0-100% gradient over 30 mins
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-75bae4e445954411bf67e0c82a299972
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09346806B2

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