Urea → HCID 178518523, compound

HRID 2174991Notes

Reaction equation

HRID 2174991 reaction equation
[NH2:1][C:2]([NH2:4])=[O:3].C([O:7][C:8](=O)[CH:9]([F:15])[C:10](OCC)=[O:11])C.CC[O-].[Na+]>CCO>[F:15][C:9]1[C:8]([OH:7])=[N:1][C:2]([OH:3])=[N:4][C:10]=1[OH:11]

Participants

5

Procedure

To a heterogeneous mixture of urea (641 mg, 10.67 mmol) and diethylfluoromalonate (1.96 g, 10.67 mmol) in EtOH (11 mL) was added 2.68 M NaOEt in EtOH (7.96 mL, 21.34 mmol). The mixture was heated at reflux for 60 h and then allowed to cool to room temperature. The mixture was filtered and the cake was then dissolved in warm water and the resulting solution was acidified with concentrated HCl to pH 2. The mixture was allowed to cool to room temperature and then cooled in an ice bath before filtering. The cake was washed with water and dried to afford 5-fluoropyrimidine-2,4,6-triol as a slightly off white solid (1.45 g, 93%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 60 h
  3. filtrationThe mixture was filtered
  4. dissolutionthe cake was then dissolved in warm water
  5. temperatureto cool to room temperature
  6. temperaturecooled in an ice bath
  7. filtrationbefore filtering
  8. washThe cake was washed with water
  9. customdried

Sources & evidence

ORD record
ord-87580e50cf0d4827abdfb45525448ac0
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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