Sodium Hydroxide → {4-[((2-Methoxyethyl){4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl}amino)methyl]-2-methylphenoxy}acetic acid

HRID 1269687Notes

Reaction equation

HRID 1269687 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:22][C:23]1[CH:35]=[CH:34][C:26]([O:27][CH2:28][C:29]([O:31]CC)=[O:30])=[C:25]([CH3:36])[CH:24]=1)[C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:9]=[CH:8][N:7]=1.[OH-].[Na+]>CO.O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:22][C:23]1[CH:35]=[CH:34][C:26]([O:27][CH2:28][C:29]([OH:31])=[O:30])=[C:25]([CH3:36])[CH:24]=1)[C:6]1[N:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=2)[CH:9]=[CH:8][N:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58622875Ethyl {4-[((2-methoxyethyl){4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl}amino)methyl]-2-methylphenoxy}acetate

Product 1

HCID 18448287{4-[((2-Methoxyethyl){4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl}amino)methyl]-2-methylphenoxy}acetic acidYield 94.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl {4-[((2-methoxyethyl){4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl}amino)methyl]-2-methylphenoxy}acetate (80 mg, 0.16 mmol) in methanol (1.5 mL) and tetrahydrofuran (1.5 mL) was added 2M sodium hydroxide (1.5 mL). The resulting mixture was stirred at room temperature for 1 h. The solvents were removed in vacuo and the residue was diluted with water (10 mL) acidified with 2M HCl and extracted ethyl acetate (2×30 mL). The organic solution was dried (MgSO4) and the solvents removed in vacuo, to afford the title compound as a cream solid (72 mg).

Workup

  1. customThe solvents were removed in vacuo
  2. additionthe residue was diluted with water (10 mL)
  3. extractionextracted ethyl acetate (2×30 mL)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-706dd3b262014ab2bcf0da1ee554925d
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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