N2-Methyl-2,3-pyridinediamine

λ/-Methyl-3-nitropyridin-2-amine (58.14 g, 0.38 mol) was dissolved in 1 , 2 dimethoxyethane (400 mL) under vigorous stirring. The obtained solution was refluxed with activated charcoal (2.9 g) for 2 h and kept overnight at room temperature. The reaction apparatus was flushed with dry nitrogen, and the catalyst (Pd/C 10percent, 1.75 g) was added. The mixture was heated to 40 A solution of 1 g (4 mmol) of N-methyl-3-nitro-2-aminopyridine, 1.57 mL of hydrazine hydrate and 0.33 g of ferric chloride448mL ethanol, add a small amount of activated carbon, reflux at 80 for 5h, hot filter, the filtrate steamed, dark green solid production0.8 g (yield: 91.04percent).Palladium (0.924 g, 0.868 mmol) was added to a three necked 1 L round bottom flask equipped with a condenser and flow of N2, and it was wet by adding a few mL of water. Then, N-methyl-3-nitropyridin-2-amine (19.0 g, 124 mmol) dissolved in ethanol (130 mL) was added. Hydrazine (15.41 ml, 496 mmol) was added to the above solution dropwise over a period of 20 minutes with continuous stirring. The reaction was exothermic, and 3/4 gas evolved during the reaction. The reaction mixture was stirred at room temperature for about 2 h. The color of the reaction changed from yellow to colorless. Completion of the reaction was checked by TLC. Pd was filtered on a tightly packed Celite3-Amino-2-chloropyridine (400 mg, 3.1 mmol) and copper sulfate pentahydrate (78 mg, 0.31 mmol, 0.10 eq.) were added to a microwave pressure vessel with 40percent methylamine in water (2.33 ml) and heated at 160 °C for 1 h. The crude product was cooled to RT and filtered through Celite. The crude mixture was treated with aqueous sodium carbonate, extracted with EtOAc (2x), dried over anhydrous NaSO4 , filtered, and dried under vacuum. After purification by column chromatography, using a solvent gradient from hexane to EtOAc, the desired compound 22 was isolated as orange solid (70percent)N2 -methylpyridine-2, 3-diamine (66 mg, 0.54 mmol) and 1, 1'-carbondiimidazole (130.3 mg, 0.80 mmol, 1.5eq) was dissolved in THF and stirred at RT under argon overnight. The solvent of the crude product mixture was evaporated under vacuum and the residue was recrystallized twice from water to give fluffy pink long crystals of the desired product (70percent)86c) 3-methyl-1, 3-dihydro-2H-imidazo[4, 5-b]pyridin-2-one A solution of N2-methylpyridine-2, 3-diamine (7 g) and CDI (13.82 g) in THF (100 mL) was refluxed for 5 h. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with 0percent-100percent EtOAc in hexane) to give 3-methyl-1, 3-dihydro-2H-imidazo[4, 5-b]pyridin-2-one (7 g) as a light brown solid.MS (API+): [M+H]+ not detected.1H NMR (300 MHz, DMSO-d6) delta 3.30 (3H, s), 6.96-7.01 (1H, m). 7.24-7.34 (1H, m), 7.90-7.98 (1H, m).B. 2-N-methyl-2, 3-diaminopyridine The nitro compound of A above is reduced catalytically in the presence of 10% palladium on charcoal in ethanol. The residue, after removal of solvent, is recrystallized in either benzene or cyclohexane to give 86% yield, melting point 98-9 C. Analysis for: C6 H9 N3: Calculated: C, 58.51; H, 7.37; N, 34.12. Found: C, 58.29; H, 7.26; N, 33.66.3-Amino-2-chloropyridine (400 mg, 3.1 mmol) and copper sulfate pentahydrate (78 mg, 0.31 mmol, 0.10 eq.) were added to a microwave pressure vessel with 40% methylamine in water (2.33 ml) and heated at 160 C for 1 h. The crude product was cooled to RT and filtered through Celite. The crude mixture was treated with aqueous sodium carbonate, extracted with EtOAc (2x), dried over anhydrous NaSO4 , filtered, and dried under vacuum. After purification by column chromatography, using a solvent gradient from hexane to EtOAc, the desired compound 22 was isolated as orange solid (70%)A mixture of

Molecular Weight:123.16
XLogP3:0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:123.079647300
Monoisotopic Mass:123.079647300
Topological Polar Surface Area:50.9
Heavy Atom Count:9
Complexity:84.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes