Carbon Dioxide → Pyrimidine-5-carboxylic acid

HRID 1720877Notes

Reaction equation

HRID 1720877 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[N:11][CH:12]=1.[C:13](=[O:15])=[O:14].S(=O)(=O)(O)O>C1COCC1>[N:9]1[CH:8]=[C:7]([C:13]([OH:15])=[O:14])[CH:12]=[N:11][CH:10]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 1118Sulfuric AcidHCID 783445-BromopyrimidineHCID 178418339Butyllithium

Product 1

HCID 78346Pyrimidine-5-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-100 °C

Procedure

n-Butyllithium (1.6M in hexane, 6.9 ml, 11 mmol) was added to dry THF (10 ml) and the solution was cooled to -100° C. A solution of 5-bromopyrimidine (1.59 g, 10 mmol) in dry THF (50 ml) was added slowly. After 15 min at -80° to -100° C., the mixture was added dropwise onto solid carbon dioxide in dry THF. After warming to room temperature, the mixture was made slightly acidic with dilute sulphuric acid. The solid was filtered off and extracted with ethanol. The extract was filtered and evaporated and the residue was re-extracted with methanol. Evaporation of solvent gave the title compound (1.48 g, 100%).

Workup

  1. temperatureAfter warming to room temperature
  2. filtrationThe solid was filtered off
  3. extractionextracted with ethanol
  4. filtrationThe extract was filtered
  5. customevaporated
  6. extractionthe residue was re-extracted with methanol
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-0be5871cb1c546d7942cdf626d6d7e50
Source dataset
uspto-grants-1996_04
Patent number
US05508288

Reaction notes

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