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

HRID 475721노트

반응식

HRID 475721 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 174Ethylene Glycol용매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2bf927a7ae0046eca44869718d36c643
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637525B2

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