Sodium Hydroxide → 7-Oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidine-2-carboxylic acid

HRID 1409315Notes

Reaction equation

HRID 1409315 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]2[CH:8]=[C:9]([C:11]([O:13]CC)=[O:12])[N:10]=[C:4]2[NH:3]1.[OH-].[Na+]>C(O)C>[O:1]=[C:2]1[CH2:7][CH2:6][N:5]2[CH:8]=[C:9]([C:11]([OH:13])=[O:12])[N:10]=[C:4]2[NH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 136377291Ethyl 7-oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidine-2-carboxylate

Product 1

HCID 1363772927-Oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidine-2-carboxylic acidYield 191%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 7-oxo-5,6,7,8-tetrahydroimidazo[1,2-a]pyrimidine-2-carboxylate (1.711 mmol, 0.358 g) was dissolved in ethanol (5 ml) and cooled to 0° C. 1N solution of NaOH (5 ml) was slowly added. The resulting mixture was heated to 60° C. for 1.5 h. Ethanol was evaporated, the residue diluted with tert-butyl methyl ether and acidified with 2 N HCl solution under cold conditions. The mixture was stirred for overnight. DCM and water was added and the precipitate was filtered. Phases in the filtrate were separated and the water phase was evaporated. The residue from water and precipitate were combined. 0.592 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 2.73 (t, 2H), 4.12 (t, 2H), 7.58 (s, 1H), 11.09 (bs, 1H).

Workup

  1. temperatureThe resulting mixture was heated to 60° C. for 1.5 h
  2. customEthanol was evaporated
  3. additionthe residue diluted with tert-butyl methyl ether
  4. additionDCM and water was added
  5. filtrationthe precipitate was filtered
  6. customPhases in the filtrate were separated
  7. customthe water phase was evaporated

Sources & evidence

ORD record
ord-fb3396441d934b279d90529fab98908f
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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