Water → 3-(5-Hexenyl)-1-methylthymine

HRID 361519

Reaktionsgleichung

Reaktionsgleichung von HRID 361519
[H-].[Na+].[CH3:3][N:4]1[CH:12]=[C:10]([CH3:11])[C:8](=[O:9])[NH:7][C:5]1=[O:6].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[CH2:19].O>CS(C)=O>[CH2:19]([N:7]1[C:8](=[O:9])[C:10]([CH3:11])=[CH:12][N:4]([CH3:3])[C:5]1=[O:6])[CH2:18][CH2:17][CH2:16][CH:15]=[CH2:14]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 759066-Bromo-1-hexeneHCID 959611,5-Dimethyl-2,4(1H,3H)-pyrimidinedione

Produkt 1

HCID 232959493-(5-Hexenyl)-1-methylthymineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

This example illustrates a synthesis of 3-(5,6-Oxidohexyl)-1-methylthymine (inventive compound no. 1906). Sodium hydride (343 mg, 14 mmol) was added to a stirring solution of 1-methylthymine (Sigma, 2.00 g, 14 mmol) in dimethylsulfoxide (30 mL). After 15 minutes, 6-bromo-1-hexene (Lancaster, 2.30 g, 14 mmol) was added and stirring continued for 69 hours. The reaction mixture was then poured into water (100 mL) and extracted with dichloromethane (4×50 mL). The combined organic layers were washed with saturated aqueous salt solution (40 mL) and dried over sodium sulfate. The solvent was evaporated under vacuum to give a residue which was crystallized in dichloromethane/ethyl ether to yield 2.80 g (88% yield) 3-(5-hexenyl)-1-methylthymine (inventive compound no. 1905).

Aufarbeitung

  1. waitcontinued for 69 hours
  2. extractionextracted with dichloromethane (4×50 mL)
  3. washThe combined organic layers were washed with saturated aqueous salt solution (40 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under vacuum
  6. customto give a residue which
  7. customwas crystallized in dichloromethane/ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0637c68438cb4737aa0348b7680386f2
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866576

Verknüpfte Notizen

Wird geladen…