ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Methylpyridine 5-Amino-2-methylpyridine

5-Amino-2-methylpyridine

Product Name5-Amino-2-methylpyridine
CAS3430-14-6
MFC6H8N2
MW108.14
EINECS625-232-5
MOL File3430-14-6.mol

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
form	Powder
pka	6.89±0.10(Predicted)
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)

Safety Information

Hazard Codes	Xn,Xi,C
Risk Statements	22-37/38-41-36/37/38-34-24/25
Safety Statements	26-36/39-45-36/37/39-36-27-36/37
RIDADR	UN2811
WGK Germany	3
Hazard Note	Harmful
HazardClass	6.1
PackingGroup	III
HS Code	29333999
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Dam. 1 Skin Irrit. 2 STOT SE 3

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

21203-68-9

80287-53-2

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

Chemical Properties

Safety Information

Usage And Synthesis

Preparation Products And Raw materials

5-Amino-2-methylpyridine Supplier

5-Amino-2-methylpyridine manufacturers

Related Product Information