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Potassium Carbonate → 6-Bromo-9-[(4-methoxyphenyl)methyl]purine

HRID 525006
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 525006
[Br:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1>CN(C=O)C>[Br:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 178419477HCID 178419477, Verbindung

Produkt 1

HCID 596273846-Bromo-9-[(4-methoxyphenyl)methyl]purineAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.00 g (5.02 mmol) of 6-bromo-9H-purine (purchased from Aldrich; cat. no. 104981) was suspended in 10 mL of DMF and potassium carbonate (2.08 g, 15.05 mmol) was added. The mixture was stirred at room temperature for 20 minutes and then 1-(chloromethyl)-4-methoxybenzene (1.40 mL, 10.06 mmol) were added. The reaction mixture was stirred at 45° C. overnight. Then the mixture was evaporated to dryness and the residue was partitioned between water and dichloromethane. The organic layer was washed with water and brine, dried over magnesium sulphate, filtered and the solvent was removed in vacuum. The product was purified by flash chromatography (0% to 50% hexane/AcOEt) to yield 447 mg (28%) of the title compound.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at 45° C. overnight
  2. customThen the mixture was evaporated to dryness
  3. customthe residue was partitioned between water and dichloromethane
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent was removed in vacuum
  8. customThe product was purified by flash chromatography (0% to 50% hexane/AcOEt)

Quellen und Nachweise

ORD-Eintrag
ord-69563e657f71439cbee8fdb7473cc8e6
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09340547B2

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