Ammonium Hydroxide → Tert-butyl 4-(3-amino-5-bromopyrazin-2-yl)piperazine-1-carboxylate
Reaktionsgleichung
[Br:1][C:2]1[N:3]=[C:4](Cl)[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[OH-].[NH4+:23]>O>[NH2:23][C:4]1[C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=[C:2]([Br:1])[N:3]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
A 300 mL pressure vessel was charged with tert-butyl 4-(5-bromo-3-chloropyrazin-2-yl)piperazine-1-carboxylate (5.0 g, 13 mmol) and concentrated ammonium hydroxide (60 mL). The vessel was sealed and the reaction mixture was magnetically stirred at 120° C. for 12 h. After the reaction mixture was cooled to room temperature, the vessel was opened and the resulting mixture was poured into water (100 mL) and extracted with CH2Cl2 (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with 3% EtOAc in CH2Cl2 (containing 2% Et3N), to afford 2.4 g (51%) of the product as a white solid. MS m/z: 358 (M+H+).
Aufarbeitung
- customThe vessel was sealed
- temperatureAfter the reaction mixture was cooled to room temperature
- extractionextracted with CH2Cl2 (50 mL×3)
- dry with materialThe combined organic layers were dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by flash column chromatography on silica gel with 3% EtOAc in CH2Cl2 (containing 2% Et3N)
Quellen und Nachweise
- ORD-Eintrag
- ord-301547f3284445478baddb8395d08e18
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08569300B2
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