Methanol → Methyl pyrimidine-5-carboxylate

HRID 1681867Notes

Reaction equation

HRID 1681867 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[CH:4]=[N:3][CH:2]=1.[CH3:10]O>>[CH3:10][O:8][C:7]([C:5]1[CH:6]=[N:1][CH:2]=[N:3][CH:4]=1)=[O:9]

Participants

3

Reactant 2

HCID 887MethanolHCID 78346Pyrimidine-5-carboxylic acid

Product 1

HCID 253902Methyl pyrimidine-5-carboxylateYield 77%

Procedure

Crude pyrimidine-5-carboxylic acid (2.4 g, 19.38 mmol) was suspended in 100 ml methanol in a round bottom flask fitted with a reflux condenser, drying tube, and a dropping funnel, and 2.8 ml thionyl chloride was added dropwise with stirring. The suspension was stirred and refluxed overnight; then cooled to room temperature and the solvents evaporated in vacuo. Ice cold water (50 ml) was added, basified to pH 8 (sat. NaHCO3), and extracted with chloroform (3×50 ml). The organics were dried (MgSO4), filtered and evaporated in vacuo to yield 2.07 g crude yellow crystals (77%).

Workup

  1. customfitted with a reflux condenser
  2. customdrying tube, and a dropping funnel
  3. addition2.8 ml thionyl chloride was added dropwise
  4. stirringThe suspension was stirred
  5. temperaturerefluxed overnight
  6. customthe solvents evaporated in vacuo
  7. additionIce cold water (50 ml) was added
  8. extractionextracted with chloroform (3×50 ml)
  9. dry with materialThe organics were dried (MgSO4)
  10. filtrationfiltered
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-502c9498087542d6a9fda80e143b2939
Source dataset
uspto-grants-1992_12
Patent number
US05175166

Reaction notes

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