Dichloromethane → 1-methyl-6-trifluoromethyl-3-(6-amino4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

HRID 277401

Reaktionsgleichung

Reaktionsgleichung von HRID 277401
[NH2:1][C:2]1[C:7]([O:8]C)=[C:6]([Cl:10])[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]1=[O:24].C(Cl)Cl>ClCCCl>[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:10])[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]1=[O:24]

Komponenten

4

Edukt 2

HCID 6344DichloromethaneHCID 183145373-(2-Amino-4-chloro-6fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)pyrimidinedione

Produkt 1

HCID 120569121-methyl-6-trifluoromethyl-3-(6-amino4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneAusbeute 62,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

3-(2-Amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (1.1 g, 2.7 mmol) was dissolved in 50 ml of anhydrous 1,2-dichloroethane and 3.4 g (10.8 mmol) of borontribromide imethylsulfide complex was added to the solution. The solution was refluxed for 16 hr and methylene chloride (100 ml) was added. Washing with water followed by drying (anhydrous sodium sulfate) and removal of the solvent afforded a residue which was triturated with ether to afford the title compound (0.6 g).

Aufarbeitung

  1. addition3.4 g (10.8 mmol) of borontribromide imethylsulfide complex was added to the solution
  2. temperatureThe solution was refluxed for 16 hr
  3. washWashing with water
  4. customby drying
  5. custom(anhydrous sodium sulfate) and removal of the solvent
  6. customafforded a residue which
  7. customwas triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-5a7f1aac39f3483da73a2db568028b8f
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355799B1

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