Ethanol → HCID 14517724, compound

HRID 1464308Notes

Reaction equation

HRID 1464308 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][S:7][C:8]1[N:13]=[C:12](O)[C:11]([CH2:15][C:16]([O:18]CC)=O)=[CH:10][N:9]=1.C(O)C.[CH3:24][NH2:25]>CO>[CH3:6][S:7][C:8]1[N:9]=[CH:10][C:11]2[CH2:15][C:16](=[O:18])[N:25]([CH3:24])[C:12]=2[N:13]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6329MethylamineHCID 24813Phosphorus oxychlorideHCID 178470739HCID 178470739, compound

Product 1

HCID 14517724HCID 14517724, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phosphorus oxychloride (59.0 g) was added to 4.84 g (21.2 mmoles) of ethyl 2-methylthio-4-hydroxy-pyrimidine-5-acetate, and the mixture was heated under reflux for 3 hours. The reaction mixture was concentrated under reduced pressure, and after adding chloroform, neutralized with an aqueous solution of sodium hydrogen carbonate. The chloroform layer was concentrated under reduced pressure. To the concentrate were added 20 ml of ethanol and 3.48 g (44.9 mmoles) of a 40 methanol solution of methylamine, and the mixture was reacted at 100 ° C. for 5 hours in an autoclave. The solvent was evaporated under reduced pressure, and after adding water, the mixture was extracted with chloroform. The chloroform layer was concentrated under reduced pressure, treated with activated carbon in ethanol, and recrystallized to give 1.50 g (yield 36%) of the desired compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionafter adding chloroform
  5. concentrationThe chloroform layer was concentrated under reduced pressure
  6. customthe mixture was reacted at 100 ° C. for 5 hours in an autoclave
  7. customThe solvent was evaporated under reduced pressure
  8. additionafter adding water
  9. extractionthe mixture was extracted with chloroform
  10. concentrationThe chloroform layer was concentrated under reduced pressure
  11. additiontreated with activated carbon in ethanol
  12. customrecrystallized

Sources & evidence

ORD record
ord-53fd5ad55c56471f847116f0c0a168e2
Source dataset
uspto-grants-1994_04
Patent number
US05304555

Reaction notes

Loading…