4-Methyl-2,6-pyridinediamine

General procedure: 4-Methylpyridine-2, 6-diamine (1). Method A: To a suspension of 4-methylpyridine (15 g, 161.1 mmol) in mineral oil (220 mL) sodium amide (27.0 g, 483.3 mmol, 3 equivs) was added and stirred over night at room temperature. The homogeneous suspension was then heated to 130 °C for 15 min whereupon hydrogen evolution started. The temperature was raised stepwise within 30 min to 160 °C, the light brown colour of the suspension changed to dark brown and the mixture formed a foam-like solid. Within 30 minthe mixture was heated to 200 °C, and release of hydrogen started, whereupon the colour changed to black. After 3 h at 215 °C hydrogen release was finished and the starting material was completely consumed as monitored by TLC (EE/MeOH/AcOH 10:1:0.1). The mixture was cooled to room temperature, the black solid was collected by filtration, and washed with petroleum ether (5x 100 mL).Silica gel (100 g) and EtOH (96 percent, 130 mL) were carefully added to the black solid in a bottom flask and evaporated after 20 min to dryness. Then the solid was added to the top of a suction strainer with conditioned silica gel (300 g; EE), equated with a gradient from EE to EE/iPrOH (8:1) and the product fraction was evaporated. The brown residue was recrystallized from tert-butyl-methyl ether/di-isopropyl ether affording 13.1 g of 1 as grey crystals (66 percent). Method B: This compound was prepared analogously to 1 with 2-amino-4-methylpyridine (15 g, 138.7 mmol) and sodium amide (16.2 g, 416.1mmol, 3 equivs) as starting material. Yield: 13.2 g (76 percent). Mp: 100-102 °C. 1H NMR (DMSO-d6) δ: 5.46 (s, 2H, Py), 5.21 (s, 4H, NH2), 1.95 (s, 3H, CH3). 13C{1H} NMR (DMSO-d6) δ: 158.7 (Py), 148.1 (Py), 96.2(Py), 20.7 (CH3). HRMS (ESI): [M+H]+, found 124.0869. C6H9N3 requires 124.0875.A solution of 4-methylpyridine (9.31 g, 0.10 mol) in tetralin (50 mL) was added to a solution of sodium amide (9.33 g, 0.24 mol) in tetralin (100 mL) at 130 °C. After the addition, the mixture was heated to 195

Molecular Weight:123.16
XLogP3:0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:123.079647300
Monoisotopic Mass:123.079647300
Topological Polar Surface Area:64.9
Heavy Atom Count:9
Complexity:84.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes