Sodium Hydroxide → 4-(2-chlorophenyl)-2-[5-(trifluoromethyl)-2H-tetrazol-2-yl]methylpyrimidine-5-carboxylic acid

HRID 1958086Notes

Reaction equation

HRID 1958086 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][N:11]=[C:10]([CH2:19][N:20]2[N:24]=[N:23][C:22]([C:25]([F:28])([F:27])[F:26])=[N:21]2)[N:9]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=[C:10]([CH2:19][N:20]2[N:24]=[N:23][C:22]([C:25]([F:26])([F:27])[F:28])=[N:21]2)[N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67125210ethyl 4-(2-chlorophenyl)-2-[5-(trifluoromethyl)-2H-tetrazol-2-yl]methylpyrimidine-5-carboxylate

Product 1

HCID 671252154-(2-chlorophenyl)-2-[5-(trifluoromethyl)-2H-tetrazol-2-yl]methylpyrimidine-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An amount of 1.74 g (4.21 mmol) of ethyl 4-(2-chlorophenyl)-2-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}pyrimidine-5-carboxylate was dissolved in 12 ml of ethanol and the solution was admixed dropwise at 0° C. with 45% strength aqueous sodium hydroxide solution (5.05 mmol). The reaction was stirred for a further hour and warmed to RT. The ethanol was then removed under reduced pressure and the residue was admixed with ice-water (10 ml). The aqueous phase was extracted with ethyl acetate. The organic phase was discarded. Then the aqueous phase was adjusted to a pH of 3 using hydrochloric acid, and again extracted with ethyl acetate (3×20 ml). The combined organic phases were dried over sodium sulphate.

Workup

  1. customThe ethanol was then removed under reduced pressure
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. extractionagain extracted with ethyl acetate (3×20 ml)
  4. dry with materialThe combined organic phases were dried over sodium sulphate

Sources & evidence

ORD record
ord-55ab3ccd554846b2b458bbf2e1a1472c
Source dataset
uspto-grants-2013_04
Patent number
US08410106B2

Reaction notes

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