Triacetoxyperiodinane → HCID 86619637, compound

HRID 733175Notes

Reaction equation

HRID 733175 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][C:36]([CH3:39])=[C:35]([CH3:40])[CH:34]=2)[N:30]=[C:29]([C:41]#[N:42])[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][C:36]([CH3:39])=[C:35]([CH3:40])[CH:34]=2)[N:30]=[C:29]([C:41]#[N:42])[N:28]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 69046468HCID 69046468, compound

Product 1

HCID 86619637HCID 86619637, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (4.2 g) was added to a solution of 4-(3-hydroxy-propyl)-6-(3,4-dimethylphenyl)-pyrimidine-2-carbonitrile (2.0 g) in dichloromethane (100 mL), and the resulting suspension stirred at room temperature for 45 min. The mixture was then washed with water (3×100 mL), dried over sodium sulphate, and evaporated at reduced pressure. The residue was flashed on silica gel using Petrol/EtOAc (2:1) to afford 4-(3-oxo-propyl)-6-(3,4-dimethylphenyl)-pyrimidine-2-carbonitrile as a white solid (1.9 g).

Workup

  1. washThe mixture was then washed with water (3×100 mL)
  2. dry with materialdried over sodium sulphate
  3. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-8cf55950a93c428492b5cd510b0cea5b
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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