Acetic Acid → 4,6-dichloro-2-(2-pyridinyl)pyrimidine
Reaktionsgleichung
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[N:12]=[CH:11][N:10]=1.O.C(O)(=O)C.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(OCC)C>[N:5]1[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=1[C:11]1[N:12]=[C:13]([Cl:15])[CH:14]=[C:9]([Cl:8])[N:10]=1Komponenten
Reaktionsbedingungen
- Temperatur
- -30 °C
Versuchsvorschrift
nButyllithium (1.5 M in hexanes/1.53 mL, 2.3 mmol) was added dropwise to a solution of 4-bromopyridine (200 μL, 2.08 mmol) and in diethyl ether (20 mL)−78° C. After 30 minutes, the reaction mixture was warmed to −30° C. and 4,6-dichloropyrimidine (283 mg, 1.9 mmol) was added. The reaction mixture was allowed to warm to 0° C. over 60 min after which water (2 mmol) and acetic acid (4 mmol) were added followed by DDQ (431 mg, 1.9 mmol). After 30 minutes, the reaction mixture was diluted with diethyl ether (30 mL) and washed three times with aqueous 3M NaOH. the organic layer was dried over MgSO4. Filtration and removal of volatiles under reduced pressure yielded a brown gummy solid which was purified by flash chromatography to afford 2-pyridyl-4,6-dichloropyrimidine as a white solid (0.261 mg, 61%). 1H NMR: (CDCl3) δ 7.40, 1H, s; 8.23, 2H, d; 8.80, 2H, d.
Aufarbeitung
- additionwere added
- waitAfter 30 minutes
- washwashed three times with aqueous 3M NaOH
- dry with materialthe organic layer was dried over MgSO4
- filtrationFiltration and removal of volatiles under reduced pressure
- customyielded a brown gummy solid which
- customwas purified by flash chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-ed763e16b8e04ab893f60c74cece211f
- Quelldatensatz
- uspto-grants-2006_05
- Patentnummer
- US07037916B2
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