Triacetoxyperiodinane → HCID 57839116, compound

HRID 733180Notes

Reaction equation

HRID 733180 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([C:27]1[CH:28]=[C:29]([C:33]2[CH:38]=[C:37]([CH2:39][CH2:40][CH2:41][OH:42])[N:36]=[C:35]([C:43]#[N:44])[N:34]=2)[CH:30]=[CH:31][CH:32]=1)([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl.CCOC(C)=O>[C:23]([C:27]1[CH:28]=[C:29]([C:33]2[CH:38]=[C:37]([CH2:39][CH2:40][CH:41]=[O:42])[N:36]=[C:35]([C:43]#[N:44])[N:34]=2)[CH:30]=[CH:31][CH:32]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57839121HCID 57839121, compound

Product 1

HCID 57839116HCID 57839116, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dess-Martin periodinane (679 mg) was added to a solution of 4-(3-tert-butyl-phenyl)-6-(3-hydroxy-propyl)-pyrimidine carbonitrile (394 mg) in DCM (5 ml) and the resulting suspension was stirred at room temperature for 45 mins. Reaction mixture was diluted with EtOAc (100 ml) then washed with water (2×100 ml). Organic layer was dried over MgSO4 and concentrated in vacuo. The residue was columned on silica gel using petrol and ethyl acetate (1:1) as eluent to generate 4-(3-tert-butyl-phenyl)-6-(3-oxo-propyl)-pyrimidine-2-carbonitrile as a pale yellow solid (266 mg).

Workup

  1. customReaction mixture
  2. washthen washed with water (2×100 ml)
  3. dry with materialOrganic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6bfc5405b0984dbf8468e7c04f62313b
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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