Sodium hydride → 2-butyl-3-[4-[(1-carbomethoxy) (1-phenyl)methoxy]-3-chlorophenyl]methyl-6-methylquinazolin-4(3H)-one

HRID 257825Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 257825
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH3:16])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[Cl:19][C:20]1[CH:37]=[C:36]([CH2:38]Br)[CH:35]=[CH:34][C:21]=1[O:22][CH:23]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:24]([O:26][CH3:27])=[O:25]>CN(C=O)C>[CH2:1]([C:5]1[N:14]([CH2:38][C:36]2[CH:35]=[CH:34][C:21]([O:22][CH:23]([C:24]([O:26][CH3:27])=[O:25])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:20]([Cl:19])[CH:37]=2)[C:13](=[O:15])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:16])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 19385604Methyl 2-(2-chloro-4-bromomethylphenoxy)-2-phenylacetateHCID 178441839HCID 178441839, Verbindung

Produkt 1

HCID 199348532-butyl-3-[4-[(1-carbomethoxy) (1-phenyl)methoxy]-3-chlorophenyl]methyl-6-methylquinazolin-4(3H)-oneAusbeute 52,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a half suspension of 62 mg (0.287 mmol) of the product of Step A of Example 1 in 1.0 mL of anhydrous DMF was added 12 mg (1.05 eq) of a 60% oil dispersion of sodium hydride and the reaction mixture was stirred under an N2 atmosphere. After stirring 10 minutes at room temperature, a solution of 0.127 g (1.2 eq) of the product of Step B dissolved in 1.0 mL DMF was added to the solution of the anion. The reaction mixture was then stirred overnight, then partitioned between water and ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and evaporated in vacuo. The residual oil was purified on a silica gel flash chromatography column eluted with 30% ethyl acetate/hexane to afford 76 mg (52%) of the title compound.

Aufarbeitung

  1. stirringAfter stirring 10 minutes at room temperature
  2. additionwas added to the solution of the anion
  3. stirringThe reaction mixture was then stirred overnight
  4. custompartitioned between water and ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residual oil was purified on a silica gel flash chromatography column
  10. washeluted with 30% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-39e927e176c74d328f5c9169e3bed87a
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264439

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