Pyridine → 2-Amino-3-bromo-5-(4-methoxyphenyl)pyrazine

HRID 1034592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1034592
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][N:3]=1.N1C=CC=CC=1.[Br:22]Br>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:7]([Br:22])=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 24408BromineHCID 156743865-(4-Methoxyphenyl)pyrazin-2-amine

Produkt 1

HCID 715237102-Amino-3-bromo-5-(4-methoxyphenyl)pyrazineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a solution of 2-amino-5-(4-mcthoxyphenyl)pyrazinc 16a (0.35 g, 1.7 mmol) and pyridine (0.20 mL, 2.6 mmol) in chloroform (20 mL), bromine (Br2) (0.13 mL, 2.6 mmol) was added dropwise in chloroform (3 mL) at −10° C. After 6 h stirring at room temperature, the reaction mixture was washed with water, the organic layer dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography using dichloromethane-EtOAc (90:10 v/v) as eluent, to obtain 0.33 g of 17a as an brown solid (mp 166-170° C., 70% yield). 1H-NMR (CDCl3): 3.83 (s, 3H), 5.04 (br s, 2H), 6.92-6.96 (m, 2H), 7.76-7.80 (m, 2H), 8.31 (s, 1H). GC-MS (EI): m/z 279,281 (M1, 100).

Aufarbeitung

  1. washthe reaction mixture was washed with water
  2. dry with materialthe organic layer dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fa0d033ad63b4d21ba822ff8ba9e0442
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546147B2

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