Sodium Hydroxide → {4-[(Butyl{5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl}amino)methyl]-2-methylphenoxy}acetic acid

HRID 1269704Notes

Reaction equation

HRID 1269704 reaction equation
[CH2:1]([N:5]([CH2:23][C:24]1[CH:36]=[CH:35][C:27]([O:28][CH2:29][C:30]([O:32]CC)=[O:31])=[C:26]([CH3:37])[CH:25]=1)[C:6]1[C:11]([CH3:12])=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[N:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>CO.O1CCCC1>[CH2:1]([N:5]([CH2:23][C:24]1[CH:36]=[CH:35][C:27]([O:28][CH2:29][C:30]([OH:32])=[O:31])=[C:26]([CH3:37])[CH:25]=1)[C:6]1[C:11]([CH3:12])=[C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=2)[N:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58622901Ethyl {4-[(butyl{5-methyl-6-[4-(trifluoromethyl)phenyl] pyrimidin-4-yl}amino)methyl]-2-methylphenoxy}acetate

Product 1

HCID 18448388{4-[(Butyl{5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl}amino)methyl]-2-methylphenoxy}acetic acidYield 99.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl {4-[(butyl{5-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-4-yl}amino)methyl]-2-methylphenoxy}acetate (190 mg, 0.37 mmol) in methanol (4 mL) and tetrahydrofuran (4 mL) was added 2M sodium hydroxide (4 mL). The resulting mixture was stirred at room temperature for 2 h. The solvents were removed in vacuo and the residue was diluted with water (20 mL), acidified with 2M HCl and extracted ethyl acetate (50 mL). The organic solution was washed with brine (20 mL), dried (MgSO4) and the solvents removed in vacuo, to afford the title compound as a white foam (180 mg).

Workup

  1. customThe solvents were removed in vacuo
  2. additionthe residue was diluted with water (20 mL)
  3. extractionextracted ethyl acetate (50 mL)
  4. washThe organic solution was washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-d7d0d4ca95084f3b9759e015da7ab248
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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