5-BROMO-4-METHYL-PYRIDINE-2,3-DIAMINE
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5-BROMO-4-METHYL-PYRIDINE-2,3-DIAMINE
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CAS No:
41230-93-7
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Formula:
C6H8BrN3
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Chemical Name:
5-BROMO-4-METHYL-PYRIDINE-2,3-DIAMINE
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Synonyms:
5-bromo-4-methyl-2,3-Pyridinediamine;2,3-diamino-5-bromo-4-methylpyridine;5-BROMO-4-METHYL-PYRIDINE-2,3-DIAMINE;5-Bromo-2,3-diamino-4-methylpyridine;5-broMo-4-Methylpyridine-2
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CAS No:
5-BROMO-4-METHYL-PYRIDINE-2,3-DIAMINE Use and Manufacturing
5-Bromo-4-methyl-3-nitropyridin-2-amine (700.0 mg, 3.02 mmol), Fe (1680.0 mg, 30.20 mmol) and conc. HCl (50.0 μL) were added to EtOH (2.8 mL) and water (0.7 mL). The suspension was stirred at 100° C. for 30 minutes. The reaction mixture was cooled to room temperature, filtered through celite and then distilled under reduced pressure. The residue was purified by column chromatography (MeOH:DCM=1:40) on silica. The fractions containing the product were collected and evaporated to obtain brown solid compound of 5-bromo-4-methylpyridin-2, 3-diamine (550.0 mg, 90percent). [0843] LCMS ESI(+): 202 (M+1), 204 (M+3) [0844] (0.21g, 1mmol) was dissolved in a mixture of EtOH - H2O; to this was added aqueous glyoxal 40% (0.2ml, 4mmol) and the resulting mixture was refluxed for 1h. Upon cooling to room temperature, water was then added. The product was separated, filtered and washed with excess water yielded 7-bromo-8-methylpyrido[2, 3-b]pyrazine as a sufficiently enough pure material (0.21g) for the next step.General procedure: A mixture of 2, 3-diaminopyridine in diethyl oxalate (10 mL/1 mmol phenyldiamine) was heated to reflux for 4 h before cooled to room temperature. The resulted solid was filtered, washed with ethyl acetate and 95% ethanol, decolorized with activated charcoal and recrystallized in water and DMF or DMSO to give 5-azaquinoxalinediones as white solid. 5.2.2.29 7-Bromo-8-methyl-1, 4-dihydropyrido[2, 3-b]pyrazine-2, 3-dione (29) The title compound was prepared from 2-amino-4-methyl-5-bromopyridine according to the general procedure as white solid (279 mg, 10.9%). IR (KBr) nu 3032, 2854, 2762, 1697, 1609, 1435, 1379 cm-1; 1H NMR (400 MHz, DMSO-d6) delta 2.45 (3H, s, CH3), 8.19 (1H, s, H-6), 11.58 (1H, brs, NH-1), 12.40 (1H, brs, NH-4); 13C NMR (100 MHz, DMSO-d6) delta 16.68, 116.67, 121.61, 131.80, 138.28, 142.51, 155.18, 155.31; HRMS-EI C8H6BrN3O2 calcd [M+H]+ 255.9722, found 255.9723.
Computed Properties
Molecular Weight:202.05
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:200.99016
Monoisotopic Mass:200.99016
Topological Polar Surface Area:64.9
Heavy Atom Count:10
Complexity:120
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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5-BROMO-4-METHYL-PYRIDINE-2,3-DIAMINE
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