Hydrochloric Acid → 2-Chloro-9-methyl-6-((S)-3-methylmorpholin-4-yl)-9H-purine-8-carbaldehyde
Reaktionsgleichung
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[N:3]=1.CN(CCN(C)C)C.[Li]CCCC.CN([CH:35]=[O:36])C.Cl>C1COCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:35]=[O:36])[N:8]2[CH3:11])=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[N:3]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -40 °C
Versuchsvorschrift
To a solution of 2-chloro-9-methyl-6-((S)-3-methylmorpholin-4-yl)-9H-purine (500 mg, 1.67 mmol) and TMEDA (419 μL, 2.80 mmol) in THF (10 mL) at −78° C. was added n-BuLi (1.12 mL, 2.80 mmol, 2.5M solution in hexanes). The resulting mixture was allowed to warm to −40° C. and stir for 30 min then cooled back to −78° C. before the addition of DMF (435 μL, 5.61 mmol). The reaction mixture was allowed to stir at −78° C. for 30 min then poured onto 1M HCl. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with H2O and brine, then dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, EtOAc:cyclohexane, 0-50%) affording the title compound as a white solid (450 mg, 81%). LCMS (method H): RT 3.28 min [M+H]+ 296.3
Aufarbeitung
- stirringto stir at −78° C. for 30 min
- extractionThe aqueous phase was extracted with EtOAc
- washthe combined organic phases were washed with H2O and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customThe resulting residue was purified by column chromatography (Si—PCC, EtOAc:cyclohexane, 0-50%)
Quellen und Nachweise
- ORD-Eintrag
- ord-a529b28a37244ecb8bbc55718ab35df0
- Quelldatensatz
- uspto-grants-2013_03
- Patentnummer
- US08394796B2
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