StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Benzyl Bromide → 5-hexynyluracil

HRID 1783598
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1783598
I[C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH:10]#[C:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:24]([C:28]1[O:37][C:31]2[CH:32]=[N:33][C:34](=[O:36])[NH:35][C:30]=2[CH:29]=1)[CH2:25][CH2:26][CH3:27]>CN(C=O)C.[OH-].[K+]>[C:10]([C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1)#[C:11][CH2:12][CH2:13][CH2:14][CH3:15].[CH2:24]([C:28]1[O:37][C:31]2[CH:32]=[N:33][C:34](=[O:36])[NH:35][C:30]=2[CH:29]=1)[CH2:25][CH2:26][CH3:27].[CH2:16]([N:35]1[C:30]2[CH:29]=[C:28]([CH2:24][CH2:25][CH2:26][CH3:27])[O:37][C:31]=2[CH:32]=[N:33][C:34]1=[O:36])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 7498Benzyl BromideHCID 127321-HexyneHCID 696725-IodouracilHCID 69060553HCID 69060553, Verbindung

Produkt 3

HCID 116799645-hexynyluracilHCID 69060553HCID 69060553, Verbindung
HCID 69065535
HCID 69065535, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 14797Potassium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

As above, 5-hexynyluracil and 6-n-butylfuranopyrimidin-2-one was prepared from 3.0 g of 5-iodouracil and 3.0 mL of 1-hexyne at 50° C. for 24 hours. Triethylamine solvent was completely distilled off at reduced pressure and a pale yellow slurry was obtained. This slurry was dissolved in 50.0 mL of DMF containing 0.70 g of KOH, and the resulting dark red solution was heated in an oil bath at 65° C. for 10 minutes. Then, 3.0 mL of benzylbromide was added to the red solution and the reaction was allowed to proceed under an Ar atmosphere until complete benzylation of 6-n-butylfuranopyrimidin-2-one to yield 1-benzyl-6-n-butylfuranopyrimidin-2-one. This alkylation took approximately 9 hours and it was monitored by TLC, as both 6-n-butylfuranopyrimidin-2-one and 1-benzyl-6-n-butylfuranopyrimidin-2-one are fluorescent under UV light but have significantly different Rf values in various solvent systems including EtOAc MeOH/Hexanes:10/1/4 and EtOAc/Ether:2/1. Once the alkylation was complete, DMF solvent was distilled off under reduced pressure and 50.0 mL of dry acetone was added to the resulting slurry to precipitate potassium bromide that was removed by gravity filtration. The filtrate was evaporated to a dark red viscous oil that was dissolved in 40.0 mL of chloroform and extraction was performed with 5% aqueous solution of EDTA (sodium salt) 2×40.0 mL and then once with 40.0 mL of distilled water.

Aufarbeitung

  1. distillationTriethylamine solvent was completely distilled off at reduced pressure
  2. customa pale yellow slurry was obtained

Quellen und Nachweise

ORD-Eintrag
ord-8e381f6d16db417595dcaa7f6ee26e2a
Quelldatensatz
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07501429B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion