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

HRID 2038180Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2038180
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, Verbindung2×

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

N2-Butyl-8-(methyloxy)-9H-purine-2,6-diamine trifluoroacetic acid salt (for example, as prepared for Intermediate 8) (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 minutes. The mixture was cooled to room temperature, 1-bromo-4-chlorobutane (commercially available, for example, from Aldrich) (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 min. 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 min
  9. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-01b7eea13f46412e88bc5534ee537bff
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575340B2

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