Potassium Carbonate → Methyl 2-([2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenylthio}pyrimidin-4-yl]oxy}propionate

HRID 1862237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1862237
[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[SH:22].C(=O)([O-])[O-].[K+].[K+].Cl[C:30]1[N:35]=[C:34]([O:36][CH:37]([C:39]([O:41][CH3:42])=[O:40])[CH3:38])[CH:33]=[CH:32][N:31]=1>C(#N)C>[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:17])([F:18])[F:19])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[S:22][C:30]1[N:35]=[C:34]([O:36][CH:37]([CH3:38])[C:39]([O:41][CH3:42])=[O:40])[CH:33]=[CH:32][N:31]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 120567412-Chloro-4-[1-(methoxycarbonyl)ethoxy]pyrimidineHCID 186192703-(4-Chloro-2-fluoro-5-sulfanylphenyl)-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Produkt 1

HCID 18619236Methyl 2-([2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenylthio}pyrimidin-4-yl]oxy}propionateAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

0.40 g of 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenyl mercaptan was dissolved in 6 ml of acetonitrile, to this solution was added 0.31 g of potassium carbonate, and the mixture was stirred for 30 minutes, then, 0.29 g of 2-chloro-4-[1-(methoxycarbonyl)ethoxy]pyrimidine was added and the mixture was stirred for 3 hours. This reaction solution was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.46 g of methyl 2-([2-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenylthio}pyrimidin-4-yl]oxy}propionate [present compound 6-2].

Aufarbeitung

  1. stirringthe mixture was stirred for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6550ebd7c2434a1bbb05773d82a8606e
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06537948B1

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