1,10-Phenanthroline → 5-Methoxy-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine

HRID 917472Notes

Reaction equation

HRID 917472 reaction equation
I[C:2]1[C:3]([NH2:14])=[CH:4][C:5]([CH: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]([CH: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 589627075-Iodo-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine

Product 1

HCID 589627065-Methoxy-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamineYield 61%

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 1.05 g (3.10 mmol) 5-iodo-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine, 59 mg (0.31 mmol) copper(I) iodide, 112 mg (0.62 mmol) 1,10-phenanthroline and 2.02 g (6.19 mmol) cesium carbonate in 5 ml methanol was heated at 130° C. for 2×3 min in a microwave oven. The resulting mixture was then cooled to room temperature and concentrated in vacuo. Flash chromatography (methanol/dichloromethane/triethylamine) afforded 394 mg (57%) 5-methoxy-2-(tetrahydro-pyran-4-yl)-pyridin-4-ylamine as a red crystalline solid. ES-MS m/e (%): 209 (M+H+, 100).

Workup

  1. temperatureThe resulting mixture was then cooled to room temperature
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e580b5d62ac74b898c9b9f0c8d95895a
Source dataset
uspto-grants-2007_09
Patent number
US07273865B2

Reaction notes

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