Hydrochloric Acid → 4-(4-Fluorophenyl)-2-hydroxy-6-methylpyrimidine

HRID 635891

Reaction equation

HRID 635891 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([CH2:8][C:9](=O)[CH3:10])=O)=[CH:4][CH:3]=1.[NH2:14][C:15]([NH2:17])=[O:16].Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O.C(O)C>[F:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]2[CH:8]=[C:9]([CH3:10])[N:17]=[C:15]([OH:16])[N:14]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 11430Potassium CarbonateHCID 4326551-(4-Fluoro-phenyl)-butane-1,3-dione

Product 1

HCID 1784227144-(4-Fluorophenyl)-2-hydroxy-6-methylpyrimidineYield 46.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5 g of 4-fluorobenzoylacetone, 1.66 g of urea, 25 ml of ethanol, and 3.8 ml of concentrated hydrochloric acid was refluxed for 20 hours. This reaction mixture was cooled, poured into iced water, made basic with aqueous solution of potassium carbonate, and neutralized with acetic acid. The crystals that separated out were collected by filtration, washed with isopropyl ether, and dried to provide 2.65 g of pale yellow crystals. m.p. 265-268° C.

Workup

  1. temperaturewas refluxed for 20 hours
  2. temperatureThis reaction mixture was cooled
  3. customThe crystals that separated out
  4. filtrationwere collected by filtration
  5. washwashed with isopropyl ether
  6. customdried

Sources & evidence

ORD record
ord-0c87bdaf0e5c4bbc85733afaad7cc70b
Source dataset
uspto-grants-2001_02
Patent number
US06191149B1

Linked notes

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