Hydrochloric Acid → 4,6-Dimethyl-2-(3-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid

HRID 1692378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1692378
C([O:3][C:4]([C:6]1[C:7]([CH3:23])=[N:8][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[N:10][C:11]=1[CH3:12])=[O:5])C.[OH-].[K+].Cl>C(OCCO)C.O>[CH3:12][C:11]1[C:6]([C:4]([OH:5])=[O:3])=[C:7]([CH3:23])[N:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[N:10]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 669015424,6-Dimethyl-2-(3-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid ethyl ester

Produkt 1

HCID 627447164,6-Dimethyl-2-(3-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acidAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167501012-Ethoxyethanol-waterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 5.21 g (16.1 mmol) of 4,6-dimethyl-2-(3-trifluoromethyl-phenyl)-pyrimidine-5-carboxylic acid ethyl ester in 165 ml of 2-ethoxyethanol/H2O (9:1) was added 2.62 g=40.2 mmol of potassium hydroxide (86%); then, the reaction mixture was heated up to reflux in an oil bath of 150° C. After 4 hours, it was poured into crashed ice, acidified with HCl (25% in water) and extracted three times with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated to give 4.29 g (90%) of the crude title compound as off-white solid. MS: 295.3 ([M−H]−).

Aufarbeitung

  1. temperaturethen, the reaction mixture was heated up
  2. additionit was poured
  3. extractionextracted three times with CH2Cl2
  4. washthe organic phases were washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-692ca07f96564bfd986b26ed6ee8006d
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153805B2

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