Dimethylformamide → 1,2,3,4-Tetrahydro-2-[5-(3,4-dimethoxyphenyl)-pyrimidin-2-yl]-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one

HRID 988308

Reaktionsgleichung

Reaktionsgleichung von HRID 988308
[H-].[Na+].[CH2:3]1[O:11][C:10]2[CH:9]=[CH:8][C:7]([CH:12]3[C:24]4[NH:23][C:22]5[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=5)[C:16]=4[CH2:15][CH2:14][N:13]3[C:25]3[N:30]=[CH:29][C:28]([C:31]4[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=4)=[CH:27][N:26]=3)=[CH:6][C:5]=2[O:4]1.CN(C=[O:45])C>>[CH3:40][O:39][C:33]1[CH:32]=[C:31]([C:28]2[CH:29]=[N:30][C:25]([N:13]3[CH2:14][C:15]4[C:16](=[O:45])[C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=5[NH:23][C:24]=4[CH:12]3[C:7]3[CH:8]=[CH:9][C:10]4[O:11][CH2:3][O:4][C:5]=4[CH:6]=3)=[N:26][CH:27]=2)[CH:36]=[CH:35][C:34]=1[O:37][CH3:38]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 110494301-Benzo[1,3]dioxol-5-yl-2-[5-(3,4-dimethoxy-phenyl)-pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-beta-carboline

Produkt 1

HCID 103016221,2,3,4-Tetrahydro-2-[5-(3,4-dimethoxyphenyl)-pyrimidin-2-yl]-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one

Versuchsvorschrift

Sodium hydride (60% in mineral oil, 40 mg, 1.0 mmol) and 1-(3,4-methylenedioxyphenyl)-2-[5-(3,4-dimethoxyphenyl)-pyrimidin-2-yl]-2,3,4,9-tetrahydro-1H-β-carboline (218 mg, 0.43 mmol) (prepared as in Example 13) in DMF (10 mL, anhydrous) were stirred at room temperature for 30 min. Dry air was then bubbled through the solution for 16 h. Ethyl acetate (100 mL) and saturated NaHCO3 were added, the organic phase was washed with water, brine, and dried with MgSO4. Solvent was evaporated and the residue purified by chromatography (silica gel, ethyl acetate) to yield the product as a white solid.

Aufarbeitung

  1. customDry air
  2. customwas then bubbled through the solution for 16 h
  3. additionEthyl acetate (100 mL) and saturated NaHCO3 were added
  4. washthe organic phase was washed with water, brine
  5. dry with materialdried with MgSO4
  6. customSolvent was evaporated
  7. customthe residue purified by chromatography (silica gel, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-37f5c5b3f8044fb889ae2eaff6ac1f79
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06635638B2

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