Benzyl Chloride → 9-Benzyl-2-pentyladenine

HRID 377584

Reaktionsgleichung

Reaktionsgleichung von HRID 377584
[NH2:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]#[N:8].[C:9]([NH2:16])(=O)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH2:17]([N:3]1[CH:4]=[N:5][C:6]2[C:2]1=[N:1][C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N:16][C:7]=2[NH2:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

7

Edukt 4

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 12332HexanamideHCID 787775-amino-1H-imidazole-4-carbonitrile

Produkt 1

HCID 193560959-Benzyl-2-pentyladenine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
210 °C

Versuchsvorschrift

A mixture of 4-amino-5-cyanoimidazole (1.09 g, 11 mmol) and hexaneamide (4.39 g, 38 mmol) was heated at 210° C. for 15 h under N2 atmosphere. After cooling, the residue was dissolved in a mixture of DMF (200 ml) and water (50 ml). Benzyl chloride (3 ml) and K2CO3 (3 g) was added to the mixture, and heated at 70° C. for 6 h. Solvent was evaporated under vacuum, the residue was extracted by CH2Cl2. The resulting organic layer was evaporated under vacuum. 9-benzyl-2-pentyladenine was obtained by the purification of the residue by column chromatography (CH2Cl2 :MeOH=100:1-50:1). Bromine (2 ml) was added to the mixture of 9-benzyl-2-hexyladenine and NaOAc (5 g) in ACOH (40 ml) within an ice bath, and the mixture was heated at 70° C. for 6 h. Solvent was evaporated under vacuum, the residue was extracted by EtOAc. The resulting organic layer was evaporated under vacuum, 9-benzyl-8-bromo-2-pentyladenine was obtained by the purification of the residue by column chromatography (CH2Cl2 :MeOH=100:1). A mixture of 9-benzyl-8-bromo-2-pentyladenine and conc.HCl (20 ml) was refluxed for 6 h. After cooling, aqueous NH3 was added to neutralize and crystallize the product (pH=8), and the desired compound was collected by filtration (0.25 g, Yield: 8%).

Aufarbeitung

  1. temperatureAfter cooling
  2. temperatureheated at 70° C. for 6 h
  3. customSolvent was evaporated under vacuum
  4. extractionthe residue was extracted by CH2Cl2
  5. customThe resulting organic layer was evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8979a20551f64a62b127c1a10ecde08c
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06028076

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