Hydrochloric Acid → 4-(Difluoromethyl)-2-(pentafluoroethyl)pyrimidine-5-carboxylic acid

HRID 1843064Notes

Reaction equation

HRID 1843064 reaction equation
[F:1][CH:2]([F:21])[C:3]1[C:8]([C:9]([O:11]CC)=[O:10])=[CH:7][N:6]=[C:5]([C:14]([F:20])([F:19])[C:15]([F:18])([F:17])[F:16])[N:4]=1.[OH-].[Na+].Cl>C(O)C>[F:21][CH:2]([F:1])[C:3]1[C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]=[C:5]([C:14]([F:20])([F:19])[C:15]([F:16])([F:17])[F:18])[N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86660090HCID 86660090, compound

Product 1

HCID 866600764-(Difluoromethyl)-2-(pentafluoroethyl)pyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.15 g (3.59 mmol) of ethyl 4-(difluoromethyl)-2-(pentafluoroethyl)pyrimidine-5-carboxylate are dissolved in 4 ml of ethanol. 5.39 ml (10.8 mmol) of 2M sodium hydroxide solution are added and the reaction mixture is stirred for four hours at room temperature. 2M hydrochloric acid is added to establish a pH of 2-3. The resulting solid is filtered off with suction, washed with a small amount of water and triturated with cyclohexane. This gives 870 mg of 4-(difluoromethyl)-2-(pentafluoroethyl)pyrimidine-5-carboxylic acid (83%) as a white solid.

Workup

  1. filtrationThe resulting solid is filtered off with suction
  2. washwashed with a small amount of water
  3. customtriturated with cyclohexane

Sources & evidence

ORD record
ord-0e129529d673458ab613216f76625cbf
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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