Triacetoxyperiodinane → HCID 57786225, compound

HRID 1628879Notes

Reaction equation

HRID 1628879 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=4[CH3:22])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH2:23][OH:24])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:23]=[O:24])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=3[CH3:22])[CH2:12][CH2:13][CH2:14][N:7]21

Participants

5

Reactant 2

HCID 159087Triacetoxyperiodinane3×HCID 57786365HCID 57786365, compound

Product 1

HCID 57786225HCID 57786225, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [9-chloro-1-(4-bromo-2-methylphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol (4.68 g, 11.5 mmol) in dimethylsulfoxide (80 mL) was added Dess-Martin reagent (5.37 g, 12.7 mmol), and the mixture was stirred at room temperature for 1 h. To the reaction mixture was added Dess-Martin reagent (0.49 g, 1.15 mmol), and the mixture was stirred at room temperature for 1 h. To the reaction mixture was added Dess-Martin reagent (1.46 g, 3.45 mmol), and the mixture was stirred at room temperature for 1 h. The reaction mixture diluted with ethyl acetate, and the mixture was quenched by saturated aqueous sodium hydrogen carbonate. The solid was removed by filtration. The filtrate was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the title compound as a pale yellow powder (4.54 g, 11.2 mmol, 97%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 h
  2. stirringthe mixture was stirred at room temperature for 1 h
  3. customthe mixture was quenched by saturated aqueous sodium hydrogen carbonate
  4. customThe solid was removed by filtration
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd7df4dd1e674fdc829d69fbafb7ae08
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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