Benzene → HCID 178466938, Verbindung

HRID 1597878

Reaktionsgleichung

Reaktionsgleichung von HRID 1597878
[CH2:1]([O:3][C:4]1[CH:11]=[C:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH:9]=[CH:8][C:5]=1[CH:6]=O)[CH3:2].[CH:17]1([N:22]2[C:26]([NH2:27])=[C:25]([C:28]([NH2:30])=[O:29])[C:24]([CH2:31][CH3:32])=[N:23]2)[CH2:21][CH2:20][CH2:19][CH2:18]1.C1C=CC=CC=1.O>[Pd].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCCCCC>[CH:17]1([N:22]2[C:26]3=[N:27][C:6]([C:5]4[CH:8]=[CH:9][C:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:11][C:4]=4[O:3][CH2:1][CH3:2])=[N:30][C:28](=[O:29])[C:25]3=[C:24]([CH2:31][CH3:32])[NH:23]2)[CH2:18][CH2:19][CH2:20][CH2:21]1

Komponenten

8

Edukt 4

HCID 241BenzeneHCID 962WaterHCID 9587084-(Diethylamino)-2-ethoxybenzaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Produkt 1

HCID 178466938HCID 178466938, VerbindungAusbeute 15,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A mixture of 2-ethoxy-4-(diethylamino)benzaldehyde (7.87 g, 35.56 mmol), 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (3.95 g, 17.78 mmol), p-toluenesulfonic acid monohydrate (0.05 g), 10% palladium on carbon (0.11 g) and benzene (150 ml) was refluxed overnight with the azeotropic removal of water. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo. The residue was combined with that from a similar experimental run, and dissolved in CH2Cl2, and loaded onto a silica gel column. Elution of the column with ether/hexane (60/40) afforded a green foam which was titurated with refluxing hexane, and cooled and the product, as pale yellow needles, was collected by filtration to afford 1.19 g (8%) of 1-cyclopentyl-3-ethyl-6-[2-ethoxy-4-(diethylamino)phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 138°-139° C.

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutiondissolved in CH2Cl2
  4. washElution of the column with ether/hexane (60/40)
  5. customafforded a green foam which
  6. temperaturecooled
  7. filtrationthe product, as pale yellow needles, was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-99927a1a151947c7b17a9b1760151020
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05736548

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