Triacetoxyperiodinane → HCID 86712570, compound

HRID 72724Notes

Reaction equation

HRID 72724 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[N:28]([CH3:29])[N:27]=[CH:26][C:25]=1[CH:30]([C:32]1[C:33]([Cl:39])=[N:34][CH:35]=[N:36][C:37]=1[Cl:38])[OH:31]>C(Cl)(Cl)Cl>[Br:23][C:24]1[N:28]([CH3:29])[N:27]=[CH:26][C:25]=1[C:30]([C:32]1[C:33]([Cl:39])=[N:34][CH:35]=[N:36][C:37]=1[Cl:38])=[O:31]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86712569(5-bromo-1-methyl-1H-pyrazol-4-yl)(4,6-dichloropyrimidin-5-yl)methanol

Product 1

HCID 86712570HCID 86712570, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dess-Martin periodinane (2.26 g, 5.33 mmol) was added in portions to a solution of (5-bromo-1-methyl-1H-pyrazol-4-yl)(4,6-dichloropyrimidin-5-yl)methanol (C25) (1.20 g, 3.55 mmol) in chloroform (30 mL), and the mixture was stirred for 2 hours. After filtration, the filtrate was concentrated in vacuo, diluted with ethyl acetate (300 mL), washed with saturated aqueous sodium hydrogen sulfite solution (3×150 mL), and washed with saturated aqueous sodium carbonate solution. The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification using silica gel chromatography (Eluent: 5:1 heptane/ethyl acetate) provided the product. Yield: 1.16 g, 3.45 mmol, 97%. LCMS m/z 337.1 (M+1). 1H NMR (400 MHz, CDCl3) δ 3.97 (s, 3H), 7.92 (s, 1H), 8.90 (s, 1H).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. additiondiluted with ethyl acetate (300 mL)
  4. washwashed with saturated aqueous sodium hydrogen sulfite solution (3×150 mL)
  5. washwashed with saturated aqueous sodium carbonate solution
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification
  10. customprovided the product

Sources & evidence

ORD record
ord-1fed9eff8e69411ea95baa9a5384c34e
Source dataset
uspto-grants-2014_09
Patent number
US08829010B2

Reaction notes

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