Ammonia → 6-Methoxy-5-(4-methyl-1H-imidazol-1-YL)pyridin-2-amine

HRID 475721

Reaktionsgleichung

Reaktionsgleichung von HRID 475721
Br[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]2)=[CH:4][CH:3]=1.[NH3:16].CO>C(O)CO.O>[CH3:9][O:8][C:6]1[N:7]=[C:2]([NH2:16])[CH:3]=[CH:4][C:5]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1

Komponenten

6

Edukt 3

HCID 222AmmoniaHCID 887MethanolHCID 576093006-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine

Produkt 1

HCID 534029676-Methoxy-5-(4-methyl-1H-imidazol-1-YL)pyridin-2-amineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 174Ethylene GlycolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine (1.000 g, 3.73 mmol) and cuprous oxide (0.053 g, 0.373 mmol) in 8.3 mL of ethylene glycol was added a 7 N solution of ammonia in methanol (7.99 mL, 55.9 mmol). The reaction mixture was heated in a high-pressure vessel at 100° C. overnight. Upon cooling to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. The solvent was removed in vacuum to give 6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-amine (762.0 mg, 3.73 mmol, 100% yield) as brown semisold. LC-MS (M+H)+=205.10. 1H NMR (500 MHz, CDCl3) δ ppm 7.53 (1H, s), 7.26 (1H, d, J=8.2 Hz), 6.78 (1H, s), 6.07 (1H, d, J=8.2 Hz), 3.86 (3H, s.), 2.25 (3H, s).

Aufarbeitung

  1. temperatureUpon cooling to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2bf927a7ae0046eca44869718d36c643
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637525B2

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