1,10-Phenanthroline → 5-Methoxy-2-morpholin-4-yl-pyridin-4-ylamine

HRID 917407ノート

反応式

HRID 917407 の反応式
I[C:2]1[C:3]([NH2:14])=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:29](=O)([O-])[O-:30].[Cs+].[Cs+]>CO.[Cu]I>[CH3:29][O:30][C:2]1[C:3]([NH2:14])=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1

参加物

6

反応物 3

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 589627005-Iodo-2-morpholinopyridin-4-amine

生成物 1

HCID 589627015-Methoxy-2-morpholin-4-yl-pyridin-4-ylamine収率 50%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 887Methanol溶媒

反応条件

温度
130 °C

実験手順

A stirred suspension of 81.4 g (267 mmol) 5-iodo-2-morpholin-4-yl-pyridin-4-ylamine, 4.06 g (21.3 mmol) copper(I) iodide, 5.77 g (32.0 mmol) 1,10-phenanthroline and 174 g (533 mmol) cesium carbonate in 600 ml methanol was heated at 130° C. for 30 min in a microwave oven. The resulting mixture was then cooled to room temperature and filtered. The filtrate was concentrated in vacuo and the residue purified by flash chromatography (1/7 methanol/dichloromethane) to afford 27.7 g (50%) 5-methoxy-2-morpholin-4-yl-pyridin-4-ylamine as a dark brown crystalline solid. ES-MS m/e (%): 210 (M+H+, 100).

後処理

  1. temperatureThe resulting mixture was then cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue purified by flash chromatography (1/7 methanol/dichloromethane)

出典と根拠

ORDレコード
ord-4d2338bae6e84bcc8e8cae313aebfa72
出典データセット
uspto-grants-2007_09
特許番号
US07273865B2

反応ノート

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