Triacetoxyperiodinane → 1-[9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-one

HRID 1628701Notes

Reaction equation

HRID 1628701 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[C:32]2[N:31]=[C:30]3[N:33]([C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:38]=4[Cl:44])[CH2:34][CH2:35][CH2:36][N:29]3[C:28]=2[C:27]([CH:45]([OH:48])[CH2:46][CH3:47])=[CH:26][CH:25]=1>C(#N)C.C(=O)([O-])O.[Na+]>[Cl:23][C:24]1[C:32]2[N:31]=[C:30]3[N:33]([C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][C:38]=4[Cl:44])[CH2:34][CH2:35][CH2:36][N:29]3[C:28]=2[C:27]([C:45](=[O:48])[CH2:46][CH3:47])=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 44156374HCID 44156374, compound

Product 1

HCID 577863001-[9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-oneYield 88%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Dess-Martin reagent (1.27 g, 3.00 mmol) was added to a stirred suspension of 1-[9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]propan-1-ol (1.12 g, 2.73 mmol) in acetonitrile (23 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, concentrated in vacuo, and extracted with ethyl acetate/tetrahydrofuran. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 15-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was washed with diisopropyl ether to give the title compound as a colorless powder (980 mg, 2.40 mmol, 88%).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with ethyl acetate/tetrahydrofuran
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel eluting with a 15-50% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give the solid, which
  10. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-b54627dcc77044f596822671e60e71a4
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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