Triacetoxyperiodinane → 9-Methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehyde

HRID 1629021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1629021
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][C:25]1[C:33]2[N:32]=[C:31]3[N:34]([C:38]4[C:39]([CH3:47])=[N:40][C:41]([O:45][CH3:46])=[N:42][C:43]=4[CH3:44])[CH2:35][CH2:36][CH2:37][N:30]3[C:29]=2[C:28]([CH2:48][OH:49])=[CH:27][CH:26]=1>CS(C)=O.C(#N)C.C(=O)([O-])O.[Na+]>[CH3:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([CH:48]=[O:49])=[C:29]2[C:33]=1[N:32]=[C:31]1[N:34]([C:38]3[C:39]([CH3:47])=[N:40][C:41]([O:45][CH3:46])=[N:42][C:43]=3[CH3:44])[CH2:35][CH2:36][CH2:37][N:30]21

Komponenten

6

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 57786030[9-Methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol

Produkt 1

HCID 577857769-Methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carbaldehydeAusbeute 61,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Dess-Martin reagent (1.31 g, 3.09 mmol) was added to a stirred solution of [9-methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol (761 mg, 2.06 mmol) in dimethyl sulfoxide (0.50 mL) and acetonitrile (8.2 mL) at 0° C., and the mixture was stirred at room temperature for 3 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. 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 0-5% methanol/ethyl acetate gradient mixture. The eluate was concentrated in vacuo to give the title compound as a brown solid (467 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 0-5% methanol/ethyl acetate gradient mixture
  7. concentrationThe eluate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b8c865ea6c734ed49b4bdc64fbfe6f1c
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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