Diisopropylethylamine → trans-3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}cyclohexanol
Reaktionsgleichung
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:25][C@H:26]1[CH2:31][CH2:30][CH2:29][C@H:28]([OH:32])[CH2:27]1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]2[C:3]3[C:2]([NH:25][C@H:26]4[CH2:31][CH2:30][CH2:29][C@H:28]([OH:32])[CH2:27]4)=[N:7][CH:6]=[N:5][C:4]=3[O:8][C:9]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:12][CH:13]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
Initially charge 1.0 g (2.97 mmol) of 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine and 513 mg (approx. 4.5 mmol) of (+/−)-cis/trans-3-aminocyclohexanol (approx. 3:1 cis/trans mixture; prepared according to J. Chem: Soc. Perkin Trans. I, 1994, 537) in 2.7 ml of DMF. After adding 1.03 ml (5.94 mmol) of DIEA, heat the mixture to 120° C. for 2 h. After cooling, add to ice-water. Filter off the precipitated solid with suction, wash with water and dry under reduced pressure. Purify the crude product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1→1:2). 1.05 g (85.1% of theory) of the target product are obtained as a cis/trans mixture.
Aufarbeitung
- temperatureAfter cooling
- filtrationFilter off the precipitated solid with suction
- washwash with water
- customdry under reduced pressure
- customPurify the crude product by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 2:1→1:2)
- custom1.05 g (85.1% of theory) of the target product are obtained as a cis/trans mixture
Quellen und Nachweise
- ORD-Eintrag
- ord-db201ce1d9114c41a247cff20858f3ad
- Quelldatensatz
- uspto-grants-2012_12
- Patentnummer
- US08324222B2
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