Sodium hydride → (2-Pyrimidin-2-yl-imidazol-1-yl)-acetic Acid Methyl Ester

HRID 895666Notes

Reaction equation

HRID 895666 reaction equation
Cl.[NH:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1[N:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[H-].[Na+].[CH3:15][O:16][C:17](=[O:20])[CH2:18]Br.[NH4+].[Cl-]>C1COCC1>[CH3:15][O:16][C:17](=[O:20])[CH2:18][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1[N:8]=[CH:9][CH:10]=[CH:11][N:12]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 60984Methyl bromoacetateHCID 222603902-(1H-Imidazol-2-yl)-pyrimidine hydrochloride

Product 1

HCID 69558628(2-Pyrimidin-2-yl-imidazol-1-yl)-acetic Acid Methyl EsterYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-(1H-imidazol-2-yl)-pyrimidine hydrochloride (1.4 g, 7.7 mmol) in THF (50 mL) is added 40% NaH in mineral oil (675 mg, 15.4 mmol), the mixture is stirred at room temperature for one hour, and bromoacetic acid methyl ester (1.3 g, 8.4 mmol) is added. The reaction mixture is stirred at ambient temperature overnight. After aqueous NH4Cl solution (50 mL) is added, the mixture is extracted with ethyl acetate (20 mL×6) and CH2Cl2 (10 mL×6). The organic extracts are combined, dried over Na2SO4, and concentrated. The resulting residue is purified on a silica gel column with 100:10:1 CH2Cl2/MeOH/NH4OH as eluent to yield the titled compound (650 mg).

Workup

  1. stirringThe reaction mixture is stirred at ambient temperature overnight
  2. extractionthe mixture is extracted with ethyl acetate (20 mL×6) and CH2Cl2 (10 mL×6)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue is purified on a silica gel column with 100:10:1 CH2Cl2/MeOH/NH4OH as eluent

Sources & evidence

ORD record
ord-e7b074b98e80439d8f1683cf43168d1f
Source dataset
uspto-grants-2005_07
Patent number
US06916827B2

Reaction notes

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