Ethanol → HCID 10905333, compound

HRID 840529Notes

Reaction equation

HRID 840529 reaction equation
[F:1][C:2]1[C:3]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]([CH3:21])[C:11]2=[O:22])=[N:4][C:5](Cl)=[C:6]([Cl:8])[CH:7]=1.C(N([CH2:28][CH3:29])CC)C.[C]=[O:31].[CH2:32]([OH:34])C>>[CH2:28]([O:31][C:32]([C:5]1[N:4]=[C:3]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]([CH3:21])[C:11]2=[O:22])[C:2]([F:1])=[CH:7][C:6]=1[Cl:8])=[O:34])[CH3:29]

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 11057435HCID 11057435, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 10905333HCID 10905333, compound

Procedure

A mixture of 4 g 1-(3-fluoro-5,6-dichloro-2-pyridyl)-3-methyl-4-trifluoromethylpyrimidin-2,6-dione (Example H4), 3.4 g triethylamine and 2 g dichloro-bis(triphenylphosphine)palladium in 50 ml ethanol is pressurized in an autoclave with carbon monoxide at 180 bar and the mixture heated for about 30 hours to 101° C., leading to a pressure build-up of max. 228 bar. The heating is then switched off, the reaction mixture left to stand at 22° C. over the weekend and filtered; the filtrate is then concentrated by evaporation in a vacuum, and the residue obtained is purified over a silica gel column (eluent: n-hexane/ethyl acetate 9/1). The desired title compound is obtained as a yellowish resin.

Workup

  1. temperaturethe mixture heated for about 30 hours to 101° C.
  2. waitthe reaction mixture left
  3. customto stand at 22° C. over the weekend
  4. filtrationfiltered
  5. concentrationthe filtrate is then concentrated by evaporation in a vacuum
  6. customthe residue obtained
  7. customis purified over a silica gel column (eluent: n-hexane/ethyl acetate 9/1)

Sources & evidence

ORD record
ord-f26e44f9ae584cc3a1d79829c998e0a4
Source dataset
uspto-grants-2002_04
Patent number
US06369002B1

Reaction notes

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