Reaktion #347449

ord-db00f9dfbc74479ba32a7ec5d18cbbaf

Reaktionsgleichung

[H-].[Na+]
sodium hydride
Nc1ncnc2nc[nH]c12
adenine
O=C1c2ccccc2C(=O)N1CCCCBr
N-(4-bromobutyl)-phthalimide
Nc1ncnc2c1ncn2C=CCCN1C(=O)c2ccccc2C1=O
expected product
Ausbeute 63.3%
Nc1ncnc2c1ncn2C=CCCN1C(=O)c2ccccc2C1=O
N-[4-(6-amino-9H-purin-9-yl)-3-butenyl]-phthalimide
Ausbeute 63.3%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.STIRRINGthe mixture was stirred at ambient temperature for 74 hours
  2. 2
    Filtrationby filtering
  3. 3
    SonstigeThe solvent of the filtrate was evaporated
  4. 4
    Waschenthe precipitate was washed with ether, with water, with ethanol
  5. 5
    Trocknenagain with ether and dried
  6. 6
    workup.DISSOLUTIONThe residue was dissolved in methanol at 65° C.
  7. 7
    Temperaturchilled

Vorschrift

3.4 g of sodium hydride were added to 9.6 g of adenine in 270 ml of dimethylformamide and the mixture was stirred for 2 hours and 30 minutes. 20 g of N-(4-bromobutyl)-phthalimide were added and the mixture was stirred at ambient temperature for 74 hours, followed by filtering. The solvent of the filtrate was evaporated and the precipitate was washed with ether, with water, with ethanol, then again with ether and dried. The residue was dissolved in methanol at 65° C. and chilled to obtain 15.00 g of the expected product.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05527780uspto-grants-1996_06