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

HRID 1269705Notes

Reaction equation

HRID 1269705 reaction equation
[CH2:1]([N:5]([CH2:21][C:22]1[CH:34]=[CH:33][C:25]([O:26][CH2:27][C:28]([O:30]CC)=[O:29])=[C:24]([CH3:35])[CH:23]=1)[C:6]1[C:11]([CH3:12])=[C:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[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]([CH2:21][C:22]1[CH:34]=[CH:33][C:25]([O:26][CH2:27][C:28]([OH:30])=[O:29])=[C:24]([CH3:35])[CH:23]=1)[C:6]1[C:11]([CH3:12])=[C:10]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[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 58622872Ethyl [4-({butyl[6-(4-methoxyphenyl)-5-methylpyrimidin-4-yl]amino}methyl)-2-methylphenoxy]acetate

Product 1

HCID 18448315[4-({Butyl[6-(4-methoxyphenyl)-5-methylpyrimidin-4-yl]amino}methyl)-2-methylphenoxy]acetic acidYield 99.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [4-({butyl[6-(4-methoxyphenyl)-5-methylpyrimidin-4-yl]amino}methyl)-2-methylphenoxy]acetate (62 mg, 0.13 mmol) in methanol (2 mL) and tetrahydrofuran (2 mL), was added 2M sodium hydroxide (1 mL). After shaking for 1 h at room temperature the solvent was removed. The residue was then acidified with 0.5M HCl aq. (20 mL), before extraction into EtOAc (2×25 mL). The organic solution was washed with brine, dried (MgSO4) and the solvents removed in vacuo to afford the title compound as a pale yellow solid (58 mg).

Workup

  1. customwas removed
  2. extractionThe residue was then acidified with 0.5M HCl aq. (20 mL), before extraction into EtOAc (2×25 mL)
  3. washThe organic solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-c8137ae6231640c385d0fbd2d373541a
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

Loading…