Sodium sulfate decahydrate → HCID 57786020, Verbindung

HRID 1628913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1628913
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:31](OC)=[O:32])=[C:12]2[C:16]=1[N:15]=[C:14]1[N:17]([C:21]3[C:26]([Cl:27])=[CH:25][C:24]([O:28][CH3:29])=[CH:23][C:22]=3[Cl:30])[CH2:18][CH2:19][CH2:20][N:13]21.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>O1CCCC1.C(#N)C.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.CS(C)=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH:31]=[O:32])=[C:12]2[C:16]=1[N:15]=[C:14]1[N:17]([C:21]3[C:22]([Cl:30])=[CH:23][C:24]([O:28][CH3:29])=[CH:25][C:26]=3[Cl:27])[CH2:18][CH2:19][CH2:20][N:13]21

Komponenten

10

Edukt 4

HCID 62649Sodium sulfate decahydrateHCID 159087TriacetoxyperiodinaneHCID 21226445Aluminium lithium hydrideHCID 57786371HCID 57786371, Verbindung

Produkt 1

HCID 57786020HCID 57786020, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a suspension of lithium aluminum hydride (45.7 mg, 1.20 mmol) in tetrahydrofuran (4 mL) was added a solution of methyl 9-chloro-1-(2,6-dichloro-4-methoxyphenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (177 mg, 0.401 mmol) in tetrahydrofuran (4 mL) at 0° C., and the resultant mixture was stirred at 0° C. for 5 min. After sodium sulfate decahydrate (450 mg) was added at 0° C., the resultant mixture was filtered and concentrated in vacuo to give a crude solid. To a solution of the crude solid in acetonitrile (4 mL) and dimethylsulfoxide (0.8 mL) was added Dess-Martin reagent (204 mg, 0.481 mmol) at room temperature, and the resultant mixture was stirred at room temperature for 20 min, diluted with aqueous sodium bicarbonate and ethyl acetate, filtered and 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 a 20-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (146 mg, 0.356 mmol, 89%).

Aufarbeitung

  1. filtrationthe resultant mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customto give a crude solid
  4. filtrationfiltered
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash column chromatography on silica gel eluting with a 20-50% ethyl acetate/n-hexane gradient mixture

Quellen und Nachweise

ORD-Eintrag
ord-add9bb6e869b434d80917df754b26004
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785460B2

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