Phenol → HCID 10053125, compound

HRID 1678080Notes

Reaction equation

HRID 1678080 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].[C:14]([C:18]1[N:23]=[C:22]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32][CH2:33][N:34]3[CH:39]=[C:38]([CH3:40])[C:37](SC#N)=[N:36][C:35]3=[O:44])[CH2:26][CH2:25]2)[CH:21]=[C:20]([C:45]([F:48])([F:47])[F:46])[N:19]=1)([CH3:17])([CH3:16])[CH3:15]>C(#N)C>[C:14]([C:18]1[N:23]=[C:22]([N:24]2[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32][CH2:33][N:34]3[CH:39]=[C:38]([CH3:40])[C:37]([O:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[N:36][C:35]3=[O:44])[CH2:26][CH2:25]2)[CH:21]=[C:20]([C:45]([F:46])([F:48])[F:47])[N:19]=1)([CH3:15])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 86608508HCID 86608508, compound

Product 1

HCID 10053125HCID 10053125, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

81.3 mg (0.9 mmol) of phenol and 325.5 mg (2.4 mmol) of K2CO3 were added to 400.0 mg (0.78 mmol) of 1-(4-{4-[2-tert-butyl-6-(trifluoromethyl)pyrimidin-4-yl]piperazin-1-yl}butyl)-5-methyl-2-oxo-1,2-dihydropyrimidin-4-yl thiocyanate from Example 7.1 in 40 ml of acetonitrile and 500.0 mg of molecular sieves (3 Å). The reaction mixture was then stirred at room temperature for 12 hours. Insolubles were filtered off, methylene chloride was added to the filtrate, followed by extraction with aqueous brine. The residue after drying of the organic phase, removal of the desiccant by filtration and evaporation of the solvent in vacuo was taken up in 100 ml of diisopropyl ether and heated. The precipitate was filtered off with suction and the mother liquor was concentrated somewhat. The mother liquor was then mixed with pentane and cooled in an ice bath. The precipitated solid was filtered off with suction, washed and dried in vacuo at 40° C., resulting in 120 mg of the title compound.

Workup

  1. filtrationInsolubles were filtered off
  2. additionmethylene chloride was added to the filtrate
  3. extractionfollowed by extraction with aqueous brine
  4. customThe residue after drying of the organic phase, removal of the
  5. filtrationdesiccant by filtration and evaporation of the solvent in vacuo
  6. temperatureheated
  7. filtrationThe precipitate was filtered off with suction
  8. concentrationthe mother liquor was concentrated somewhat
  9. additionThe mother liquor was then mixed with pentane
  10. temperaturecooled in an ice bath
  11. filtrationThe precipitated solid was filtered off with suction
  12. washwashed
  13. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-5957e51c99204e568774c3db9daeff0d
Source dataset
uspto-grants-2011_08
Patent number
US08008488B2

Reaction notes

Loading…