Sodium Hydroxide → HCID 18448302, compound

HRID 1269686Notes

Reaction equation

HRID 1269686 reaction equation
[CH2:1]([N:5]([CH2:19][C:20]1[CH:32]=[CH:31][C:23]([O:24][CH2:25][C:26]([O:28]CC)=[O:27])=[C:22]([CH3:33])[CH:21]=1)[C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C1COCC1.CO>[CH2:1]([N:5]([CH2:19][C:20]1[CH:32]=[CH:31][C:23]([O:24][CH2:25][C:26]([OH:28])=[O:27])=[C:22]([CH3:33])[CH:21]=1)[C:6]1[N:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[CH:9]=[CH:8][N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 58622896Ethyl [4-({butyl[4-(4-chlorophenyl)pyrimidin-2-yl]amino}methyl)-2-methylphenoxy]acetate

Product 1

HCID 18448302HCID 18448302, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [4-({butyl[4-(4-chlorophenyl)pyrimidin-2-yl]amino}methyl)-2-methylphenoxy]acetate (178 mg, 0.38 mmol) in THF (3 mL) and MeOH (3 mL) was added NaOH (2M; 2 mL) and the resultant mixture agitated for 1.5 h. The mixture was evaporated and acidified with 2M HCl, extracted with CH2Cl2 (10 mL), EtOAc (10 mL). The aqueous was filtered, the filtered solids and solvent extracts combined and the solvent removed in vacuo to afford the title compound as a white solid (161 mg).

Workup

  1. customThe mixture was evaporated
  2. extractionextracted with CH2Cl2 (10 mL), EtOAc (10 mL)
  3. filtrationThe aqueous was filtered
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-21ddb7132e1d47d59bb5e395d5897fbb
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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