Ethanol → HCID 178441969, compound

HRID 230154Notes

Reaction equation

HRID 230154 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[N:10]=[C:9](OC2C=CC(F)=CC=2F)[C:8]([C:20](=O)[CH2:21][CH:22]([CH3:24])[CH3:23])=[CH:7][N:6]=1.CCO.[NH2:34][NH2:35]>O1CCOCC1>[F:1][C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[N:10]=[C:9]2[NH:34][N:35]=[C:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:8]2=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 59834381HCID 59834381, compound

Product 1

HCID 178441969HCID 178441969, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

1-[2,4-Bis-(2,4-difluoro-phenoxy)-pyrimidin-5-yl]-3-methyl-butan-1-one (0.427 g, 1.0 mmol) was dilloved in 10 mL of 10:1 dioxane:EtOH, and hydrazine (0.032 mL) was added. The reaction mixture was heated to 90° C. for four hours, then cooled and quenched by addition of 25 mL saturated aqueous ammonium chloride and 25 mL water. The aqueous mixture was extracted three times with 25 mL EtOAc, and the combined organic layers were washed with saturated aqueous brine, dried (Na2SO4), filtered, and evaporated under reduced pressure. The residue was eluted through silica gel using 20% EtOAc in hexanes to yield 65 mg of 6-(2,4-difluoro-phenoxy)-3-isobutyl-1H-pyrazolo[3,4-d]pyrimidine as an oil. Mass Spec. M+H=305.

Workup

  1. temperaturecooled
  2. customquenched by addition of 25 mL saturated aqueous ammonium chloride and 25 mL water
  3. extractionThe aqueous mixture was extracted three times with 25 mL EtOAc
  4. washthe combined organic layers were washed with saturated aqueous brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. washThe residue was eluted through silica gel using 20% EtOAc in hexanes

Sources & evidence

ORD record
ord-8f4f104c90054de2af40c4afffbb35da
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

Loading…