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| | 5-Amino-2-methylpyridine Basic information |
| | 5-Amino-2-methylpyridine Chemical Properties |
| Melting point | 95-99°C | | Boiling point | 238.4±20.0 °C(Predicted) | | density | 1.068±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | pka | 6.89±0.10(Predicted) | | form | Powder | | color | Off-white to orange to brown | | InChI | InChI=1S/C6H8N2/c1-5-2-3-6(7)4-8-5/h2-4H,7H2,1H3 | | InChIKey | UENBBJXGCWILBM-UHFFFAOYSA-N | | SMILES | C1=NC(C)=CC=C1N | | LogP | 0.704 | | CAS DataBase Reference | 3430-14-6(CAS DataBase Reference) |
| | 5-Amino-2-methylpyridine Usage And Synthesis |
| Chemical Properties | White to orange to brown solid | | Uses | 6-Methylpyridine-3-amine, is a heterocyclic building block used in the manufacture of various pharmaceutical compounds. It can be used for the synthesis of 2-aminoquinazoline derivatives, as a novel class of metabotropic glutamate receptor 5 negative allosteric modulators (mGluR5), leading toward a drug candidate for the treatment of l-DOPA induced dyskinesia. | | General Description | 5-Amino-2-methylpyridine is used as a pharmaceutical intermediate for Omecamtiv Mecarbil, a selective cardiac myosin activator used to improve cardiac function. | | Synthesis | To a 250 mL autoclave was added 100 mL of methanol (MeOH), 2-methyl-5-nitropyridine (15 g, 0.19 mol, 1.0 eq.) and 10% palladium/carbon catalyst (0.5 g, 3.3 wt%). The reaction mixture was stirred at room temperature for 18 h under 4 atm hydrogen pressure. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio of petroleum ether:ethyl acetate = 3:1) to confirm the completion of the reaction. Upon completion of the reaction, the reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under reduced pressure to afford 3-amino-6-methylpyridine (11.5 g, HPLC purity: 97%) as a dark red solid in 98.3% yield. | | References | [1] Patent: WO2018/208630, 2018, A1. Location in patent: Page/Page column 55
[2] Patent: US5580872, 1996, A
[3] Patent: US5733912, 1998, A
[4] Chemische Berichte, 1939, vol. 72, p. 577,579
[5] Journal of Medicinal Chemistry, 2003, vol. 46, # 22, p. 4676 - 4686 |
| | 5-Amino-2-methylpyridine Preparation Products And Raw materials |
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