Sodium ethoxide → Ethyl 2-amino-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-3-carboxylate

HRID 1170870Notes

Reaction equation

HRID 1170870 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[N:12][C:13]#[N:14])[CH3:2].C([O-])C.[Na+]>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[N:6]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]2=[N:12][C:13]=1[NH2:14])=[O:15])[CH3:2]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 15034768HCID 15034768, compound

Product 1

HCID 5200237Ethyl 2-amino-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-3-carboxylateYield 57.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound D (16.05 g, 76.7 mmol) was added to a solution of sodium ethanolate (5.20 g, 76.7 mmol, 1.0 eq.) in ethanol (500 mL) and the resulting reaction mixture was heated for 30 minutes under reflux. The solvent was removed under vacuum and the untreated product was purified by means of column chromatography (hydromatrix as the adsorbent, SiO2, DCM/3% MeOH→DCM/5% MeOH). 9.27 g of the desired product E were obtained. The columns were washed with methanol, the solvent was removed under vacuum and the residue was recrystallised by heptane in order to obtain a further 3.26 g of the desired product 2-amino-5,6,7,8-tetrahydro-imidazo[1,2-a]-pyridine-3-carboxylic-acid ethyl ester (E). In total, 12.53 g (78%) of the desired product 2-amino-5,6,7,8-tetrahydro-imidazo[1,2-a]-pyridine-3-carboxylic-acid ethyl ester (E) were obtained.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas heated for 30 minutes
  3. temperatureunder reflux
  4. customThe solvent was removed under vacuum
  5. customthe untreated product was purified by means of column chromatography (hydromatrix as the adsorbent, SiO2, DCM/3% MeOH→DCM/5% MeOH)

Sources & evidence

ORD record
ord-cc669bfb446f4c41b312e55f69540c37
Source dataset
uspto-grants-2010_11
Patent number
US07829568B2

Reaction notes

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