Cyclohexene → 4-(trifluoromethyl)pyrimidine-5-carboxylic Acid

HRID 393481Notes

Reaction equation

HRID 393481 reaction equation
C([O:8][C:9]([C:11]1[C:12]([C:18]([F:21])([F:20])[F:19])=[N:13][C:14](Cl)=[N:15][CH:16]=1)=[O:10])C1C=CC=CC=1.C1CCCCC=1>C(O)C.[Pd]>[F:21][C:18]([F:19])([F:20])[C:12]1[C:11]([C:9]([OH:10])=[O:8])=[CH:16][N:15]=[CH:14][N:13]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 2735989Benzyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate

Product 1

HCID 116080754-(trifluoromethyl)pyrimidine-5-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-chloro-4-trifluoromethyl-5-pyrimidine carboxylic acid benzyl ester in cyclohexene (3 mL, 30 mmole) and ethanol (9 mL) was treated with 10% palladium on carbon and the resulting mixture was heated to reflux for 1 h. The mixture was cooled to room temperature and filtered through a pad of Celite and concentrated to give a quantitative yield of a gummy, off-white solid. LR ES MS (C6H3F3N2O2): 191 (M−H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 1 h
  3. filtrationfiltered through a pad of Celite
  4. concentrationconcentrated
  5. customto give a quantitative yield of a gummy, off-white solid

Sources & evidence

ORD record
ord-bf9f683b458c4e4883e262084cc30e3f
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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