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Phosphorus oxychloride → (2S)-7-chloro-2-methyl-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

HRID 2408330
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2408330
O[C:2]1[N:3]=[C:4]2[NH:11][C@:10]([CH3:16])([C:12]([F:15])([F:14])[F:13])[CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.P(Cl)(Cl)([Cl:19])=O>ClCCCl>[Cl:19][C:2]1[N:3]=[C:4]2[NH:11][C@:10]([CH3:16])([C:12]([F:15])([F:14])[F:13])[CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1
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Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 136069601(2S)-7-hydroxy-2-methyl-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

Produkt 1

HCID 136069597(2S)-7-chloro-2-methyl-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a suspension of 5.6 g of (2S)-7-hydroxy-2-methyl-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one in 100 mL of 1,2-dichloroethane, are added at room temperature and under an argon atmosphere, 11 mL of phosphorus oxychloride. The resulting mixture is then heated to 70° C. After two hours of stirring and after monitoring with LC/MS, the reaction is completed. After cooling, the reaction mixture is dry evaporated under reduced pressure. The obtained residue is taken up with 5 mL of cold water and 200 mL of ethyl acetate. On the obtained mixture, 32% soda is added up to a pH=6. The organic phase is then separated and then dried on magnesium sulphate, filtered and concentrated under reduced pressure in order to obtain 6 g of (2S)-7-chloro-2-methyl-2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one including the following characteristics:

Aufarbeitung

  1. additionare added at room temperature and under an argon atmosphere
  2. temperatureAfter cooling
  3. customthe reaction mixture is dry
  4. customevaporated under reduced pressure
  5. additionOn the obtained mixture, 32% soda is added up to a pH=6
  6. customThe organic phase is then separated
  7. customdried on magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure in order

Quellen und Nachweise

ORD-Eintrag
ord-ffd53f30bb3e490192ce05f598935534
Quelldatensatz
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08815853B2

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