Azobisisobutyronitrile → tert-Butyl (5-(bromomethyl)pyrazin-2-yl)carbamate
Reaktionsgleichung
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.C1C(=O)N([Br:23])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[N:6][CH:7]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
To a solution tert-butyl 5-methylpyrazin-2-ylcarbamate (500 mg, 2.39 mmol) in CCl4 (8.0 mL) were added NBS (446 mg, 2.51 mmol) and AIBN (117 mg, 0.72 mmol). The reaction mixture was stirred for 4 hours at 80° C. after which, it was partitioned between CH2Cl2 and water. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4, celite filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography using (10% Ethyl acetate/Hexane) as a solvent to afford title compound (520 mg, 75% yield). 1H NMR (600 MHz, CDCl3) δ 9.29 (s, 1H), 8.95 (s, 1H), 8.37 (s, 1H), 4.38 (s, 2H), 1.57 (s, 9H). MS m/z: 288 [M+1].
Aufarbeitung
- customwas partitioned between CH2Cl2 and water
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with CH2Cl2
- washThe combined organic extracts were washed with brine
- dry with materialdried over MgSO4, celite
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by flash chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-fbcfee93f2a146bd9faeb9b3cf919dd8
- Quelldatensatz
- uspto-grants-2015_11
- Patentnummer
- US09180127B2
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