Potassium Carbonate → HCID 59686845, Verbindung

HRID 426111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426111
[Br:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH3:21])[CH:20]=1)[C:5]([C:7]1[NH:12][C:11](=[O:13])[NH:10][C:9](=[O:14])[C:8]=1[CH:15]([CH3:17])[CH3:16])=[O:6].Cl[CH2:23][C:24]1[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([N:31]2[C:39](=[O:40])[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]2=[O:41])[CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Li+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH3:21])[CH:20]=1)[C:5]([C:7]1[N:12]([CH2:23][C:24]2[CH:29]=[C:28]([CH3:30])[N:27]=[C:26]([N:31]3[C:39](=[O:40])[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:32]3=[O:41])[CH:25]=2)[C:11](=[O:13])[NH:10][C:9](=[O:14])[C:8]=1[CH:15]([CH3:16])[CH3:17])=[O:6]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 577518946-(3-bromo-5-methylbenzoyl)-5-isopropylpyrimidine-2,4(1H,3H)-dioneHCID 59184674HCID 59184674, Verbindung

Produkt 1

HCID 59686845HCID 59686845, VerbindungAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of (28) (351 mg, 1 mmol), (30) (287 mg, 1 mmol), anhydrous powdered potassium carbonate (138 mg, 1 mmol), and lithium iodide (134 mg, 1 mmol), was added DMF (5 ml). The mixture was stirred for overnight at room temperature. The mixture was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA: hexanes (from 1:2 to 1:1)) to afford 211 mg (35%) of a white solid; 1H NMR (200 MHz, CDCl3) δ 1.13 (3H, d, J=7.2 Hz), 1.20 (3H, d, J=7.2 Hz), 2.17-2.40 (4H, m), 2.47 (3H, s), 4.49 (1H, d, J=16.0 Hz), 5.15 (1H, d, J=16.0 Hz), 6.84 (1H, s), 6.91 (1H, s), 7.36 (1H, s), 7.53 (1H, s), 7.61 (1H, s), 7.77-7.96 (4H, m), 9.30 (1H, s).

Aufarbeitung

  1. customThe mixture was then evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent, EA: hexanes (from 1:2 to 1:1))

Quellen und Nachweise

ORD-Eintrag
ord-1bf414a94066419097343c9bbe373d44
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106064B2

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