Methyl iodide → HCID 57786158, Verbindung

HRID 1399079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1399079
[H-].[Na+].[Cl:3][C:4]1[C:12]2[N:11]=[C:10]3[N:13]([C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=4[Cl:24])[CH2:14][CH2:15][CH2:16][N:9]3[C:8]=2[C:7]([CH:25]([CH2:28][CH3:29])[CH2:26][OH:27])=[CH:6][CH:5]=1.[CH3:30]I>CN(C)C=O.[Cl-].[NH4+]>[Cl:3][C:4]1[C:12]2[N:11]=[C:10]3[N:13]([C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=4[Cl:24])[CH2:14][CH2:15][CH2:16][N:9]3[C:8]=2[C:7]([CH:25]([CH2:26][O:27][CH3:30])[CH2:28][CH3:29])=[CH:6][CH:5]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57786343HCID 57786343, Verbindung

Produkt 1

HCID 57786158HCID 57786158, VerbindungAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

Sodium hydride (60% in oil, 15.2 mg, 0.381 mmol) was added to a stirred solution of 2-[9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]butan-1-ol (108 mg, 0.254 mmol) in N,N-dimethylformamide (2.0 mL) at room temperature. After stirring 5 min, methyl iodide (71.7 mg, 0.508 mmol) was added to the mixture, and the mixture was stirred at room temperature for 5 hr. The mixture was diluted with aqueous saturated ammonium chloride, 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 10-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the solid, which was recrystallized from ethyl acetate/diisopropyl ether to give the title compound as a colorless crystal (56.1 mg, 0.128 mmol, 50%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 5 hr
  2. extractionextracted with ethyl acetate
  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 10-50% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo
  9. customto give the solid, which
  10. customwas recrystallized from ethyl acetate/diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e8a42a62c37f44ec981271d5fddc7281
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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