Triacetoxyperiodinane → HCID 86632934, compound

HRID 1628919Notes

Reaction equation

HRID 1628919 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[O:20])=[CH:17][C:16]=4[CH3:24])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH2:25][OH:26])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(#N)C.CS(C)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:15]4[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[O:20])=[CH:17][C:16]=4[CH3:24])[CH2:12][CH2:13][CH2:14][N:7]3[C:6]=2[C:5]([CH:25]=[O:26])=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57786003HCID 57786003, compound

Product 1

HCID 86632934HCID 86632934, compoundYield 78%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 4-[9-chloro-6-(hydroxymethyl)-3,4-dihydropyrimido[1,2-a]benzimidazol-1(2H)-yl]-3-methylbenzamide (390 mg, 1.05 mmol) in acetonitrile (11 mL) and dimethylsulfoxide (2.2 mL) was added Dess-Martin reagent (534 mg, 1.26 mmol) at room temperature, and the resultant mixture was stirred at room temperature for 3 h and diluted with aqueous sodium bicarbonate and aqueous sodium thiosulfate. The resultant mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate to give the title compound as a yellow solid (302 mg, 0.818 mmol, 78%).

Workup

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-78abc774bae9447997e99d13ac98e0b2
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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