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)

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

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(3430-14-6)Related Product Information

• 2,2-Dimethylbutyric acid
• 2,2-DIMETHYLVALERIC ACID
• 2,2-Dimethylbutyryl chloride
• (2-Methyl-6-trifluoromethylpyridin-3-yl)amine
• 2,6-Dimethyl-3-nitropyridine
• 2.4.6-TRIMETHYL-3-NITROPYRIDINE
• 2-Amino-3,5-dinitro-6-methylpyridine
• 5-Amino-2-methylpyridine
• Streptonigrin
• 3-AMINO-2,6-DIMETHYLPYRIDINE
• ETHYL 2-METHYL-5-NITRONICOTINATE
• 2-Amino-3-nitro-6-picoline
• Elbanizine
• 5-Amino-3-methylpyridine-2-carbonitrile,5-AMINO-3-METHYLPYRIDINE-2-CARBONITRILE,PURITY:95% MIN(HPLC)
• 2,6-Dibromopyridin-3-amine
• 2-(BOC-AMINO)-5-PICOLINE
• 3-Amino-6-fluoro-2-methylpyridine
• 3-Pyridinecarboxylicacid,2-amino-5-methyl-(9CI)