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

HRID 475721

反応式

HRID 475721 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2bf927a7ae0046eca44869718d36c643
出典データセット
uspto-grants-2014_01
特許番号
US08637525B2

関連ノート

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