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

Participants

Role	Name	HCID	Charge
Reactant	1,10-Phenanthroline	HCID 1318	—
Reactant	Cesium carbonate	HCID 10796	—
Reactant	5-Iodo-2-morpholinopyridin-4-amine	HCID 58962700	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Methanol	HCID 887	—
Product	5-Methoxy-2-morpholin-4-yl-pyridin-4-ylamine	HCID 58962701	50%

Reaction Conditions

Temperature	130 °C

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07273865B2
Source dataset	uspto-grants-2007_09
ORD ID	ord-4d2338bae6e84bcc8e8cae313aebfa72
Source note	uspto-grants-2007_09