Reaktionsgleichung
Cl[C:2]1[C:3]2[C:10]([C:11]#[N:12])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(O)(C)(C)C.CCOCC>[N:13]1([C:2]2[C:3]3[C:10]([C:11]#[N:12])=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1Komponenten
Versuchsvorschrift
To a stirred solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (54 mg/0.3 mmol) (prepared by the method of Townsend, et. al., J. Am. Chem. Soc., 1969, 91, 2102) suspended in 3.0 mL tert-Butanol was added piperidine (59 μL/0.60 mmol). The resulting mixture was then heated at reflux for 2.5 h and after cooling to room temperature, was transferred to a separatory funnel and diluted with ether (20 mL). The solution was extracted 2×10 mL with 1N HCl, the combined aqueous layers were adjusted to pH 7 with 2 N potassium hydroxide (KOH) solution forming a precipitate which was collected by filtration, washed with water and dried under reduced pressure to give 29 mg (42%) of the title compound as a colorless solid. Mp 209-211° C.; 1H NMR (400 MHz) (acetone-6) δ1.72-1.74 (m, 6H), 3.72-3.79 (m, 4H), 8.12 (s, 1H), 8.29 (s, 1H). LRMS: 228 (M+1).
Aufarbeitung
- temperatureThe resulting mixture was then heated
- temperatureat reflux for 2.5 h
- customwas transferred to a separatory funnel
- extractionThe solution was extracted 2×10 mL with 1N HCl
- customforming a precipitate which
- filtrationwas collected by filtration
- washwashed with water
- customdried under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-a5512fe3f0ee48e48a3d36c8f470212d
- Quelldatensatz
- uspto-grants-2003_08
- Patentnummer
- US06610847B2
Verknüpfte Notizen
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