Potassium Carbonate → 3-(3-{3-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pyridin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-phenyl)-acrylonitrile

HRID 426219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 426219
[CH:1]([C:4]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:5]=1[C:12]([C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]#[N:24])[CH:17]=[C:18]([CH3:20])[CH:19]=1)=[O:13])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[I-].[Li+].[C:33]1(=[O:51])[N:37]([C:38]2[CH:43]=[C:42]([CH2:44]Cl)[CH:41]=[CH:40][N:39]=2)[C:36](=[O:46])[C:35]2=[CH:47][CH:48]=[CH:49][CH:50]=[C:34]12>CN(C=O)C>[O:51]=[C:33]1[C:34]2[C:35](=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:36](=[O:46])[N:37]1[C:38]1[CH:43]=[C:42]([CH2:44][N:6]2[C:5]([C:12]([C:14]3[CH:15]=[C:16]([CH:21]=[CH:22][C:23]#[N:24])[CH:17]=[C:18]([CH3:20])[CH:19]=3)=[O:13])=[C:4]([CH:1]([CH3:3])[CH3:2])[C:9](=[O:10])[NH:8][C:7]2=[O:11])[CH:41]=[CH:40][N:39]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 591846992-[4-(Chloromethyl)-2-pyridinyl]-1H-isoindole-1,3(2H)-dioneHCID 667053903-[3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile

Produkt 1

HCID 667055303-(3-{3-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pyridin-4-ylmethyl]-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl}-5-methyl-phenyl)-acrylonitrileAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 3-[3-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile (323 mg, 1 mmol), anhydrous powdered potassium carbonate (138 mg, 1 mmol), lithium iodide (134 mg, 1 mmol), and 2-phthalimido-4-chloromethylpyridine, was added anhydrous DMF (5 ml) and the mixture was stirred for overnight at room temperature. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexane (1:1)) to afford 152 mg (27%) of a white solid. 1H-NMR (200 MHz, DMSO-d6) δ 1.01 (3H, d, J=6.8 Hz), 1.10 (3H, d, J=6.8 Hz), 2.12 (1H, m), 2.33 (3H, s), 4.76 (2H, s), 6.57 (1H, d, J=16.6 Hz), 7.25 (1H, d, J=5.2 Hz), 7.31 (1H, s), 7.61 (1H, d, J=16.6 Hz), 7.80 (1H, s), 7.88-8.02 (6H, m), 8.41 (1H, d, J=5.2 Hz), 11.72 (1H, s).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a1e0c20d22b54cae8e5ccae424321998
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106064B2

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