Lithium borohydride → [9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol

HRID 1399042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1399042
[BH4-].[Li+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:25](OC)=[O:26])=[C:8]2[C:12]=1[N:11]=[C:10]1[N:13]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])[CH2:14][CH2:15][CH2:16][N:9]21>O1CCCC1>[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]([CH2:25][OH:26])=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 4148881Lithium borohydrideHCID 57785909Methyl 9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate

Produkt 1

HCID 57785885[9-Chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanolAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium borohydride (2.12 g, 97.4 mmol) was added to a stirred solution of methyl 9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (10.0 g, 24.3 mmol) in tetrahydrofuran (80 mL) at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction was quenched by aqueous saturated ammonium chloride at 0° C., and the mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give the solid, which was washed with ethyl acetate/diisopropyl ether to give the title compound as a colorless powder (8.31 g, 21.7 mmol, 89%).

Aufarbeitung

  1. customThe reaction was quenched by aqueous saturated ammonium chloride at 0° C.
  2. extractionthe mixture was extracted 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. customto give the solid, which
  8. washwas washed with ethyl acetate/diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9daeb288f7bd49f7aa3dfbe284c0e1cc
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901141B2

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