Potassium Hydroxide → Imidazo(1,2-a)pyrimidine-2-carboxylic acid

HRID 23962Notes

Reaction equation

HRID 23962 reaction equation
[N:1]1[C:2]([C:10]([O-:12])=[O:11])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[N:6][C:5]=12.[OH-].[K+]>C(O)C>[N:1]1[C:2]([C:10]([OH:12])=[O:11])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[N:6][C:5]=12

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 6987274Imidazo[1,2-a]pyrimidine-2-carboxylate

Product 1

HCID 326100Imidazo(1,2-a)pyrimidine-2-carboxylic acidYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of ethyl 1-(imidazo[1,2-a]pyrimidine-2-carboxylate (1 g, 5.2 mmol) [Abignente, et al. Eur. J. Med. Chem. (1994) 29, 279] in ethanol (30 mL) was added 2 N aqueous KOH (10 mL, 20 mmol). The solution was heated to reflux; and after 2 h, the heating mantle was removed, the solution was allowed to cool and the solvent was removed by rotary evaporation. The residue was dissolved in water (20 mL) and acidified to pH 3 with 5 N HCl. The resulting precipitate was filtered, washed with water and dried in vacuo to give 700 mg (83%) of a tan solid.

Workup

  1. temperatureThe solution was heated to reflux
  2. customthe heating mantle was removed
  3. temperatureto cool
  4. customthe solvent was removed by rotary evaporation
  5. dissolutionThe residue was dissolved in water (20 mL)
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with water
  8. customdried in vacuo

Sources & evidence

ORD record
ord-81b55db0f6af485f8483d472d1550f6b
Source dataset
uspto-grants-2005_02
Patent number
US06855715B1

Reaction notes

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