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

HRID 874186Notes

Reaction equation

HRID 874186 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

1.74 g (4.21 mmol) of ethyl 4-(2-chlorophenyl)-2-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}pyrimidine-5-carboxylate were dissolved in 12 ml of ethanol and 45% strength aqueous sodium hydroxide solution (5.05 mmol) was added dropwise at 0° C. The reaction was stirred for a further hour and warmed to RT. The ethanol was then removed under reduced pressure, and ice-water (10 ml) was added to the residue. 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. (logP: 2.50; MH+: 385; 1H-NMR (400 MHz, DMSO, ppm): 6.59 (s, 2H), 7.48 (m, 4H), 9.27 (s, 1H).

Workup

  1. customThe ethanol was then removed under reduced pressure, and ice-water (10 ml)
  2. additionwas added to the residue
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. extractionagain extracted with ethyl acetate (3×20 ml)
  5. dry with materialThe combined organic phases were dried over sodium sulphate

Sources & evidence

ORD record
ord-bb17494753214754bc6ddae55abddd54
Source dataset
uspto-grants-2015_03
Patent number
US08980886B2

Reaction notes

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