HCID 86598743, compound → HCID 86053660, compound

HRID 419728Notes

Reaction equation

HRID 419728 reaction equation
[CH:1]1([CH:4]([C:6]2[C:7]([Cl:13])=[N:8][CH:9]=[N:10][C:11]=2[Cl:12])[OH:5])[CH2:3][CH2:2]1>CC(C)=O.[O-2].[Cr+3].[O-2].[O-2].[Cr+3]>[CH:1]1([C:4]([C:6]2[C:7]([Cl:13])=[N:8][CH:9]=[N:10][C:11]=2[Cl:12])=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 86598743HCID 86598743, compound

Product 1

HCID 86053660HCID 86053660, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 165971Chromium oxideCatalystHCID 180AcetoneSolvent

Procedure

Add chromium oxide (VI) (5.84 g, 58.4 mmoles) portion wise to cyclopropyl-(4,6-dichloro-pyrimidin-5-yl)-methanol (4.0 g, 18.2 mmoles) in 80.0 mL acetone at 0° C. and stirr for 30 min at 0° C. Next add isopropyl alcohol to quench the excess reagent and stir for another 15 min at room temperature. Cool to 0° C. and pour onto sat. NaHCO3 solution. Filter through Celite® bed, extract with ethyl acetate (3×50 mL), and wash the combined organic layers with saturated aqueous sodium chloride. Dry and concentrate under reduced to give the title compound as a colorless oil (2.0 g, Yield 50%, 9.2 mmol).

Workup

  1. customNext add isopropyl alcohol to quench the excess reagent
  2. temperatureCool to 0° C.
  3. additionpour onto sat. NaHCO3 solution
  4. filtrationFilter through Celite® bed
  5. extractionextract with ethyl acetate (3×50 mL)
  6. washwash the combined organic layers with saturated aqueous sodium chloride
  7. customDry
  8. concentrationconcentrate under reduced

Sources & evidence

ORD record
ord-76239f19b6164436b99012649c5928c7
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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