Triisopropyl borate → 2-(Dimethylamino)-4-methoxypyrimidin-5-ylboronic acid
Reaktionsgleichung
Br[C:2]1[C:3]([O:11][CH3:12])=[N:4][C:5]([N:8]([CH3:10])[CH3:9])=[N:6][CH:7]=1.[B:13](OC(C)C)([O:18]C(C)C)[O:14]C(C)C.C([Li])CCC.[Cl-].[NH4+]>C1COCC1>[CH3:9][N:8]([CH3:10])[C:5]1[N:4]=[C:3]([O:11][CH3:12])[C:2]([B:13]([OH:18])[OH:14])=[CH:7][N:6]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -70 °C
Versuchsvorschrift
To a solution of 5-bromo-4-methoxy-N,N-dimethylpyrimidin-2-amine (0.300 g, 1.29 mmol) and triisopropyl borate (0.416 mL, 1.81 mmol) in 7 mL of THF at −70° C. was added butyllithium (1.6 m in hexanes, 1.13 mL, 1.81 mmol) dropwise. The reaction stirred for 30 min at −70° C. and was allowed to warm up. At −20° C. ammonium chloride (sat.) was added. The mixture was extracted with ethyl acetate (3X). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give 250 mg of crude material, which was purified by column chromatography (5% MeOH in dichloromethane) to give 157 mg of 2-(dimethylamino)-4-methoxypyrimidin-5-ylboronic acid as a white solid. ES+=198.1 (M+H).
Aufarbeitung
- temperatureto warm up
- extractionThe mixture was extracted with ethyl acetate (3X)
- dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give 250 mg of crude material, which
- customwas purified by column chromatography (5% MeOH in dichloromethane)
Quellen und Nachweise
- ORD-Eintrag
- ord-0334a6bee2314bcfbb2b6d9dc9012b5c
- Quelldatensatz
- uspto-grants-2010_07
- Patentnummer
- US07759337B2
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