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

HRID 917407Notes

Reaction equation

HRID 917407 reaction equation
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

Participants

6

Reactant 3

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

Product 1

HCID 589627015-Methoxy-2-morpholin-4-yl-pyridin-4-ylamineYield 50%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolvent

Conditions

Temperature
130 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-4d2338bae6e84bcc8e8cae313aebfa72
Source dataset
uspto-grants-2007_09
Patent number
US07273865B2

Reaction notes

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