2-Amino-4-methoxypyridine

Pale Yellow Solid

A solution of 4-chloropyridin-2-amine (10 g, 78.1 mmol) in sodium methoxide solution (50 mL, 1M solution) in a sealed tube was heated at 145 °C for 6 h. The solvent was concentrated in vacuo resulting in residue which was purified by chromatography on silica gel, eluting with 10percent methanol in DCM to give 7.7 g, 79percent yield of the title compound as an off white solid. MS (ESj: m/z = 125.04 [M+H], 281.75 [M/2+H] LCMS: tR = 0.17 mm.Step 1 : To a solution of 4-chloropyridin-2-amine (3 g, 23.2 mmol) in DMSO (60 mL) was added sodium methoxide (12.6 g, 232 mmol) and the mixture was then stirred at 150 °C for 3 hours then poured into ice- water. The product was extracted with EtOAc (2x100 mL), and the combined organic layers were washed with water (50 mL) and brine (50 mL), dried (NaTo a solution of 4-chloropyridin-2-amine (3 g, 23.2 mmol) in DMSO (60 mL) was added sodium methoxide (12.6 g, 232 mmol) and the mixture was then stirred at 150 °C for 3 hours then poured into ice-water. The product was extracted with EtOAc (2x100 mL), and the combined organic layers were washed with water (50 mL) and brine (50 mL), dried (Na2-Amino-4-chloropyridine (970mg, 7.18mmol) was dissolved in 50mL methanol. Sodium methoxide was prepared in situ, by adding sodium (450mg, 19.6mmol) to the stirred solution. The reaction mixture was then stirred under reflux for 48 hours. TLC control indicated complete conversion. The reaction mixture was then cooled to room temperature. The pH value was adjusted to pH 8 by adding 10percent aqueous hydrochloric acid. The solvent was removed in vacuum, the remaining residue was resuspended in diethyl ether and the insoluble components were removed by filtration. The solvent was removed in vacuum. Yield 511mg, 57.4percent.

2-Amino-4-methoxypyridine is a highly selective inducible nitric oxide synthase inhibitors.

Molecular Weight:124.14
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:124.063662883
Monoisotopic Mass:124.063662883
Topological Polar Surface Area:48.1
Heavy Atom Count:9
Complexity:87.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes