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

HRID 1692378Notes

Reaction equation

HRID 1692378 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 167501012-Ethoxyethanol-waterSolvent

Conditions

Temperature
150 °C

Procedure

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]−).

Workup

  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

Sources & evidence

ORD record
ord-692ca07f96564bfd986b26ed6ee8006d
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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