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

HRID 1399373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1399373
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-7eadfa4cdc35492eacb5f87bdf8b9aaa
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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