Urea → HCID 178518523, compound

HRID 1193120Notes

Reaction equation

HRID 1193120 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-6be81dfbb4c04744ba8766d243fb6e9c
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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