7-Methyl-2-phenyloxazolo[4,5-b]pyridine → 2-Pyridinamine,3-methoxy-4-methyl-(9CI)

86 mg of the 7-methyl-2-phenyl[1,3]oxazolo[4,5-b]pyridine [159-1] was dissolved in a mixture solvent of 4 mL of tetrahydrofuran and 4 mL of ethanol, 1.64 mL of an aqueous solution of sodium hydroxide 33% was added thereto, and heated overnight under reflux. After cooling back to room temperature, the reaction solution was concentrated under reduced pressure. To the obtained residue, 5 mL of dichloromethane and 3.4 mL of an aqueous solution of sodium hydroxide 33% were added and stirred. Thereto, 28 μL of methyl iodide and 30.5 μL of Adogen 464 (phase transfer catalyst, Aldrich Corporation) were added, and stirred overnight at room temperature. Water was added, the reaction solution was extracted with chloroform, and the organic layer was washed with phosphate buffer pH 7.0, water, and saturated brine in the subsequent order. The organic layer was dried over anhydrous sodium sulfate, the insolubles were filtered, the filtrate was concentrated under reduced pressure, and the thus obtained residue was purified by preparative thin-layer chromatography, to obtain 4.2 mg of 3-methoxy-4-methylpyridin-2-amine [159-2] as a light brown solid.

1. additionwas added
2. temperatureheated overnight
3. temperatureunder reflux
4. concentrationthe reaction solution was concentrated under reduced pressure
5. additionTo the obtained residue, 5 mL of dichloromethane and 3.4 mL of an aqueous solution of sodium hydroxide 33% were added
6. additionThereto, 28 μL of methyl iodide and 30.5 μL of Adogen 464 (phase transfer catalyst, Aldrich Corporation) were added
7. stirringstirred overnight at room temperature
8. additionWater was added
9. extractionthe reaction solution was extracted with chloroform
10. washthe organic layer was washed with phosphate buffer pH 7.0, water, and saturated brine in the subsequent order
11. dry with materialThe organic layer was dried over anhydrous sodium sulfate
12. filtrationthe insolubles were filtered
13. concentrationthe filtrate was concentrated under reduced pressure
14. customthe thus obtained residue was purified by preparative thin-layer chromatography

ORD record

ord-b8422a2bac524beca64572577366b8d7

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07718801B2