Triethylamine → 7-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-4,7-diazaspiro[2.5]octane-4-carboxylic acid tert-butyl ester
Reaktionsgleichung
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.CCN(CC)CC.[C:18]([O:22][C:23]([N:25]1[CH2:32][CH2:31][NH:30][CH2:29][C:26]21[CH2:28][CH2:27]2)=[O:24])([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[C:18]([O:22][C:23]([N:25]1[CH2:32][CH2:31][N:30]([C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:29][C:26]21[CH2:27][CH2:28]2)=[O:24])([CH3:21])([CH3:19])[CH3:20]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 110 °C
Versuchsvorschrift
To commercially available 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1.0 g, 6.5 mmol) dissolved in DMF (5 ml) was added Et3N (1.3 ml, 9.8 mmol) followed by commercially available 4,7-diaza-spiro[2.5]octane-4-carboxylic acid tert-butyl ester (1.5 g, 7.2 mmol). The reaction mixture was heated for 16 hours at 110° C. After evaporation of the solvent in vacuo the crude mixture was treated with water (25 mL) and extracted with EtOAc (4×30 mL) the combined organic phases were washed with brine (2×20 mL), dried over Na2SO4, filtered and concentrated in vacuo to provide 1.5 g crude. The product was purified by flash chromatography on silica using EtOAc in heptane as eluent.
Aufarbeitung
- customAfter evaporation of the solvent in vacuo the crude mixture
- additionwas treated with water (25 mL)
- extractionextracted with EtOAc (4×30 mL) the combined organic phases
- washwere washed with brine (2×20 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto provide 1.5 g crude
- customThe product was purified by flash chromatography on silica
Quellen und Nachweise
- ORD-Eintrag
- ord-e9e66cf9828c47c7a78933a513ba95f0
- Quelldatensatz
- uspto-grants-2016_05
- Patentnummer
- US09346809B2
Notizen zur Reaktion
Wird geladen…