1,2-Diaminocyclohexane → HCID 11996714, Verbindung
Reaktionsgleichung
Br[C:2]1[CH:3]=[C:4]([C:8]2[NH:12][N:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C1(N)CCCCC1N.[NH:21]1[C:25]2=[N:26][CH:27]=[N:28][C:29]([NH2:30])=[C:24]2[CH:23]=[N:22]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu](I)I.C(OCC)(=O)C>[N:11]1[NH:12][C:8]([C:4]2[CH:3]=[C:2]([N:21]3[C:25]4=[N:26][CH:27]=[N:28][C:29]([NH2:30])=[C:24]4[CH:23]=[N:22]3)[CH:7]=[CH:6][CH:5]=2)=[CH:9][CH:10]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
5-(3-bromo-phenyl)-1H-pyrazole (0.3 g, 1.0 eq, 1.34 mmol) and cyclohexane-1,2-diamine (0.03 g, 0.2 eq, 0.27 mmol) were added to a pre-stirred mixture of 1H-Pyrazolo[3,4-d]pyrimidin-4-ylamine (0.22 g, 1.2 eq, 1.62 mmol), copper iodide (0.013 g, 0.5 eq, 0.68 mmol) and potassium phosphate (0.6 g, 2.1 eq, 2.84 mmol) in DMF (8 ml) under an inert atmosphere. The reaction mixture was then stirred at 110° C. for 24 hours, and allowed to cool to room temperature. Ethyl acetate (8 ml) was then added to the reaction mixture which was then filtered through a plug of silica, which was then washed with a further portion of ethylacetate (20 ml). The filtrate was concentrated to dryness in vacuo and the resultant residue was purified by column chromatography using DCM/MeOH (95:5) as eluent to yield the title compound as an off-white solid (0.9 mg, 0.0003 mmol, 0.2%). LCMS: [M+H]+=277, Rt=1.80 min, 93% purity.
Aufarbeitung
- temperatureto cool to room temperature
- filtrationwas then filtered through a plug of silica, which
- washwas then washed with a further portion of ethylacetate (20 ml)
- concentrationThe filtrate was concentrated to dryness in vacuo
- customthe resultant residue was purified by column chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-185a36f64512478fb6b8733d88e86fcd
- Quelldatensatz
- uspto-grants-2011_12
- Patentnummer
- US08071607B2
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