Potassium Carbonate → Ethyl 2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidine-1-yl]phenoxy}methyl)phenoxy]propionate

HRID 432558Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432558
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[OH:22].C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][C:31]1[CH:44]=[CH:43][CH:42]=[CH:41][C:32]=1[O:33][CH:34]([CH3:40])[C:35]([O:37][CH2:38][CH3:39])=[O:36]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:19])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[O:22][CH2:30][C:31]1[CH:44]=[CH:43][CH:42]=[CH:41][C:32]=1[O:33][CH:34]([CH3:40])[C:35]([O:37][CH2:38][CH3:39])=[O:36]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneHCID 11808300Ethyl 2-(2-bromomethylphenoxy)propionate

Produkt 1

HCID 18759635Ethyl 2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidine-1-yl]phenoxy}methyl)phenoxy]propionateAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Into 10 ml of N,N-dimethylformamide was dissolved 0.3 g of 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidine-1-yl]phenol; 0.159 g of anhydrous potassium carbonate was added; 0.305 g of ethyl 2-[2-(bromomethyl)phenoxy]propionate was added at room temperature under stirring and the mixture was stirred overnight at room temperature. The reaction solution was poured into a mixture of ice and a saturated aqueous ammonium chloride solution and the mixture was extracted twice with ethyl acetate. The organic layers were combined and washed once with a saturated aqueous ammonium chloride solution and once with saturated aqueous sodium chloride solution in turn, dried over magnesium sulfate and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 0.35 g of ethyl 2-[2-({2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidine-1-yl]phenoxy}methyl)phenoxy]propionate [Compound 3-2].

Aufarbeitung

  1. stirringthe mixture was stirred overnight at room temperature
  2. additionThe reaction solution was poured into a mixture of ice
  3. extractiona saturated aqueous ammonium chloride solution and the mixture was extracted twice with ethyl acetate
  4. washwashed once with a saturated aqueous ammonium chloride solution and once with saturated aqueous sodium chloride solution in turn
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9b681321d8134aeca590c3f6c83db852
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664214B1

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