Acetic Acid → HCID 178439469, compound

HRID 1588486Notes

Reaction equation

HRID 1588486 reaction equation
O=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6]CC)=O.S(O)(O)(=O)=O.[CH2:17]([NH:19][C:20]([NH2:22])=[NH:21])[CH3:18].[Na].C(O)(=O)C>C(O)C>[CH2:17]([NH:19][C:20]1[N:22]=[C:4]([OH:6])[CH:3]=[C:2]([CH2:9][CH2:10][CH3:11])[N:21]=1)[CH3:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 238498Ethyl 3-oxohexanoateHCID 5360545SodiumHCID 178464632HCID 178464632, compound

Product 1

HCID 178439469HCID 178439469, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-oxo-hexanoate (4.74 g; 30 mM) and N-ethylguanidine sulphate (4.08 g; 30 mM) were dissolved in a solution prepared by dissolving sodium (1.4 g; 0.65 g atom) in ethanol (100 ml) and the mixture was heated under reflux on the steam bath for 18 hours. Acetic acid (5 ml) was added to the cooled mixture which was stirred for 10 minutes. Insoluble material was removed by filtration and the filtrate was evaporated. The residue was partitioned between water (50 ml) and methylene chloride (50 ml). The aqueous layer was extracted twice with methylene chloride (50 ml). The combined extracts were dried and the solvent evaporated. The residue was crystallised from cyclohexane to give 2-ethylamino-4-hydroxy-6-propylpyrimidine as a solid (4.6 g; 85% yield), m.p. 108°-110° C.

Workup

  1. customprepared
  2. temperaturethe mixture was heated
  3. temperatureunder reflux on the steam bath for 18 hours
  4. customInsoluble material was removed by filtration
  5. customthe filtrate was evaporated
  6. customThe residue was partitioned between water (50 ml) and methylene chloride (50 ml)
  7. extractionThe aqueous layer was extracted twice with methylene chloride (50 ml)
  8. customThe combined extracts were dried
  9. customthe solvent evaporated
  10. customThe residue was crystallised from cyclohexane

Sources & evidence

ORD record
ord-86d86c7b98f24f19ba6bce44335e74d1
Source dataset
uspto-grants-1993_06
Patent number
US05223505

Reaction notes

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