Triacetoxyperiodinane → HCID 86619632, compound

HRID 733161Notes

Reaction equation

HRID 733161 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=2)[N:30]=[C:29]([C:43]#[N:44])[N:28]=1>ClCCl>[O:23]=[CH:24][CH2:25][CH2:26][C:27]1[CH:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:40])[F:41])[CH:34]=2)[N:30]=[C:29]([C:43]#[N:44])[N:28]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 11666681HCID 11666681, compound

Product 1

HCID 86619632HCID 86619632, compoundYield 140.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (104 mg) was added to a solution of 4-(3-hydroxy-propyl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile (50 mg) in dichloro-methane (5 mL), and the resulting suspension stirred at room temperature for 45 min. The mixture was then washed with water (3×10 mL), dried over sodium sulphate, and evaporated at reduced pressure to afford 4-(3-oxo-propyl)-6-(3-trifluoromethyl-phenyl)-pyrimidine-2-carbonitrile as a brown solid (70 mg). MS m/z 306.1 (M+1), 100%.

Workup

  1. washThe mixture was then washed with water (3×10 mL)
  2. dry with materialdried over sodium sulphate
  3. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-08d0a2b2a610475fb70d814e9ce91c3a
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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