Hydrochloric Acid → 4-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid

HRID 1242377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1242377
C([O:3][C:4]([C:6]1[C:7]([CH:22]2[CH2:24][CH2:23]2)=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C.O>[CH:22]1([C:7]2[C:6]([C:4]([OH:5])=[O:3])=[CH:11][N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:14][CH:13]=3)[N:8]=2)[CH2:24][CH2:23]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 670721284-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid ethyl ester

Produkt 1

HCID 219357274-Cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acidAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

The solutions of 3.6 g (10.7 mmol) of 4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid ethyl ester (example 27D]) in 40 ml of ethanol and of 1.07 g (26.7 mmol) of sodium hydroxide in 5 ml of H2O were mixed and then refluxed for 1 hour. After cooling to ambient temperature, 6.7 ml of 4N aqueous hydrochloric acid was added. The reaction mixture was extracted with three portions of ethyl acetate. The combined organic phases were washed with water and brine and dried over anhydrous sodium sulfate. The 4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid crystallized upon concentrating the solution by evaporation. After cooling in an ice bath, 3.08 g of white crystals were obtained (84% of theory).

Aufarbeitung

  1. temperaturerefluxed for 1 hour
  2. extractionThe reaction mixture was extracted with three portions of ethyl acetate
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe 4-cyclopropyl-2-(4-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid crystallized
  6. concentrationupon concentrating the solution
  7. customby evaporation
  8. temperatureAfter cooling in an ice bath

Quellen und Nachweise

ORD-Eintrag
ord-44587bac6dcf4d8488617d456e2d417f
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115611B2

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