Hydrochloric Acid → 4-(3,4-Dichloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyrimidine-2-carboxylic acid

HRID 1528363Notes

Reaction equation

HRID 1528363 reaction equation
C[O:2][C:3]([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C:8]([O:19][CH2:20][C:21]([F:24])([F:23])[F:22])=[CH:7][N:6]=1)=[O:4].[OH-].[Li+].Cl>O1CCCC1.O>[Cl:18][C:13]1[CH:12]=[C:11]([C:9]2[C:8]([O:19][CH2:20][C:21]([F:23])([F:24])[F:22])=[CH:7][N:6]=[C:5]([C:3]([OH:4])=[O:2])[N:10]=2)[CH:16]=[CH:15][C:14]=1[Cl:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 666787794-(3,4-Dichloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyrimidine-2-carboxylic acid methyl ester

Product 1

HCID 666787804-(3,4-Dichloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyrimidine-2-carboxylic acidYield 97.55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.79 g 4-(3,4-dichloro-phenyl)-5-(2,2,2-trifluoro-ethoxy)-pyrimidine-2-carboxylic acid methyl ester in 28 mL tetrahydrofuran was added 13 mL of a 1M solution of lithium hydroxide in water and the mixture was stirred at room temperature for 1 h. The reaction mixture was acidified by addition of 1M hydrochloric acid. The precipitate was collected by filtration washed with water and dried to constant weight under high vacuum to yield 3.561 g (97.55%) of the title compound as white solid, MS 365.0 (M−H)−.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried to constant weight under high vacuum

Sources & evidence

ORD record
ord-861c35e37c054db8aab8d788d6e59aa2
Source dataset
uspto-grants-2015_07
Patent number
US09090599B2

Reaction notes

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