Hydrochloric Acid → HCID 178517794, compound

HRID 1366385Notes

Reaction equation

HRID 1366385 reaction equation
[F:1][CH:2]([F:6])[C:3](=[NH:5])[NH2:4].Cl.[F:8][CH:9]([C:14](OC)=[O:15])[C:10](OC)=[O:11]>>[F:1][CH:2]([F:6])[C:3]1[NH:4][C:14]([OH:15])=[C:9]([F:8])[C:10](=[O:11])[N:5]=1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 2737111Dimethyl fluoromalonateHCID 26597148HCID 26597148, compound

Product 1

HCID 178517794HCID 178517794, compoundYield 61%

Conditions

Temperature
80 °C

Procedure

Sodium metal (0.91 g, 40 mmol) was dissolved in MeOH (100 mL) to form sodium methoxide. 2,2-Difluoroethanimidamide.HCl (1.73 g, 13 mmol) was added followed by dimethyl fluoropropanedioate (2.0 g, 13 mmol). The resulting solution was stirred at 80° C. for 3 hours, then cooled to room temperature. Aqueous HCl (6 mL, 6M, 36 mmol) was added and the resulting mixture was concentrated in vacuo. The remaining solid was washed with cold water and filtered yielding 2-(difluoromethyl)-5-fluoro-6-hydroxy-4(1H)-pyrimidinone (1.43 g, 61%)

Workup

  1. temperaturecooled to room temperature
  2. concentrationthe resulting mixture was concentrated in vacuo
  3. washThe remaining solid was washed with cold water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-8f306e572cce46809c6ade0901ae883b
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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