Hydrochloric Acid → 5-Cyano-4-trifluoromethyl-pyrimidin-6-one

HRID 1886143Notes

Reaction equation

HRID 1886143 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[C:10](=[O:11])[NH:9][CH:8]=[N:7][C:6]=1[C:12]([F:15])([F:14])[F:13].C(OC(=O)C)C.Cl>N1C2C(=CC=CC=2)C=CC=1.C(O)(=O)C.O.C(O)C.C(OCC)C>[C:2]([C:5]1[C:10](=[O:11])[NH:9][CH:8]=[N:7][C:6]=1[C:12]([F:15])([F:14])[F:13])#[N:3]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 1354246005-Bromo-6-(trifluoromethyl)pyrimidin-4-olHCID 178418546HCID 178418546, compound

Product 1

HCID 1360230715-Cyano-4-trifluoromethyl-pyrimidin-6-one

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolvent2×HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 7047QuinolineSolvent

Procedure

Copper(I)cyanide (80 mg) was added to a solution of 5-bromo-4-trifluoromethylpyrimidin-6-one (150 mg) in quinoline (5 ml). The reaction mixture was then heated to the reflux temperature for a period of 3 hours. After cooling to the ambient temperature, the reaction mixture was poured into dilute aqueous acetic acid, and extracted into ethyl acetate. After drying, evaporation of the solvent under reduced pressure gave a brown oil, which was subjected to chromatography on silica gel plates using ethylacetate containing acetic acid and water (250:5:1 by volume) as eluent. The desired fraction was collected, and the brown solid thus isolated was identified as a phenolic salt. This material was dissolved in ethanol, and acidified with ethanolic hydrogen chloride. Evaporation of the solvent under reduced pressure gave a brown solid which was dissolved in diethyl ether and filtered. Evaporation of the solvent under reduced pressure gave 5-cyano-4-trifluoromethyl-pyrimidin-6-one as a brown solid. IR (Nujol mull) 3100, 2920, 2235, 1730, 1700, 1680, 1600, 1440, 1330, 1210, 1160, 1130 and 958 cm-' ;

Workup

  1. temperatureThe reaction mixture was then heated to the reflux temperature for a period of 3 hours
  2. extractionextracted into ethyl acetate
  3. customAfter drying
  4. customevaporation of the solvent under reduced pressure
  5. customgave a brown oil, which
  6. customThe desired fraction was collected
  7. customthe brown solid thus isolated
  8. customEvaporation of the solvent under reduced pressure
  9. customgave a brown solid which
  10. filtrationfiltered
  11. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-58157a15c6f7475f85bb390be25fa337
Source dataset
uspto-grants-1992_09
Patent number
US05149810

Reaction notes

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