Potassium Carbonate → N2-Butyl-9-(4-chlorobutyl)-8-(methyloxy)-9H-purine-2,6-diamine

HRID 527775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527775
FC(F)(F)C(O)=O.[CH2:8]([NH: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]([NH: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]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 178448879HCID 178448879, Verbindung

Produkt 1

HCID 59252596N2-Butyl-9-(4-chlorobutyl)-8-(methyloxy)-9H-purine-2,6-diamineAusbeute 109,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

N2-Butyl-8-(methyloxy)-9H-purine-2,6-diamine trifluoroacetate (5 g, 14.27 mmol) and potassium carbonate (4.93 g, 35.7 mmol) were suspended in DMF (40 ml) and heated to 50° C. under nitrogen for 30 mins. The mixture was cooled to room temperature, 1-bromo-4-chlorobutane (1.645 ml, 14.27 mmol) was added and stirring was continued at room temperature for 20 hours. The solvent was concentrated under vacuum and the residue was partitioned between DCM (100 ml) and water (100 ml). The layers were separated using a hydrophobic frit and the aqueous phase was re-extracted with DCM (100 ml). The combined organics extracts were concentrated in vacuo and the residue purified by chromatography using a FlashMaster apparatus (100 g silica cartridge) and using a DCM:methanol 0-25% gradient over 40 mins. The desired fractions were combined and concentrated under vacuum to give the impure title compound as a yellow oil (5.1 g).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationThe solvent was concentrated under vacuum
  3. customthe residue was partitioned between DCM (100 ml) and water (100 ml)
  4. customThe layers were separated
  5. extractionthe aqueous phase was re-extracted with DCM (100 ml)
  6. concentrationThe combined organics extracts were concentrated in vacuo
  7. customthe residue purified by chromatography
  8. waitmethanol 0-25% gradient over 40 mins
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fe90c88eedb1460a9ec0ed8c9c1d935a
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346806B2

Notizen zur Reaktion

Wird geladen…