Chloride → 6-Amino-2-methoxy-4-(4-acetoxybutyl)pyrimidine

HRID 1836197

Reaktionsgleichung

Reaktionsgleichung von HRID 1836197
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[NH:5][C:4](=O)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl-].[C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25]Br)(=[O:20])[CH3:19]>CC(C)=O>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([CH2:25][CH2:24][CH2:23][CH2:22][O:21][C:18](=[O:20])[CH3:19])[CH:3]=1

Komponenten

6

Edukt 4

HCID 312ChlorideHCID 11430Potassium CarbonateHCID 784911-Butanol, 4-bromo-, 1-acetateHCID 1354042146-Amino-2-methoxy-3,4-dihydropyrimidin-4-one

Produkt 1

HCID 234990886-Amino-2-methoxy-4-(4-acetoxybutyl)pyrimidineAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Alternative Method B. A mixture of 6-amino-2-methoxy-4-pyrimidone (30 g, 212.6 mmol), K2CO3 (44 g, 318 mmol), benzyltriethylammionium chloride (20 g, 88 mmol) and 4-bromobutyl acetate (60 g, 308 mmol) in acetone (800 ml) was heated at reflux overnight. After cooling to room temperature, the insoluble salts were filtered off and the solvent was removed. The residue was purified by chromatography on silica gel with CHCl3/MeOH (100:2-100:5) as eluent. After separation of 6-amino-2-methoxy-4-(4-acetoxybutyl)pyrimidine (22.8, yield 42%), 18.7 g (yield 34.5%) of 6-amino-2-methoxy-3-(4-acetoxybutyl)-4-pyrimidone was isolated as a white solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. filtrationthe insoluble salts were filtered off
  4. customthe solvent was removed
  5. customThe residue was purified by chromatography on silica gel with CHCl3/MeOH (100:2-100:5) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-c02c628edb0048c4a13daa4ec2f86a16
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06777420B2

Verknüpfte Notizen

Wird geladen…