5-Amino-2-methoxypyridine Chemical Properties

Melting point:

29-31 °C (lit.)

Boiling point:

85-90 °C/1 mmHg (lit.)

Density 

1.575

refractive index 

n20/D 1.575(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Chloroform, Methanol (Slightly)

form 

Liquid

pka

4.33±0.10(Predicted)

color 

Yellow-brown or red to very dark red

Water Solubility 

Slightly soluble

InChI

1S/C6H8N2O/c1-9-6-3-2-5(7)4-8-6/h2-4H,7H2,1H3

InChIKey

UUVDJIWRSIJEBS-UHFFFAOYSA-N

SMILES

COc1ccc(N)cn1

CAS DataBase Reference

6628-77-9(CAS DataBase Reference)

NIST Chemistry Reference

5-Amino-2-methoxypyridine(6628-77-9)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

RTECS 

US1836000

HazardClass 

IRRITANT

HS Code 

29339900

Storage Class

10 - Combustible liquids

Hazard Classifications

Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:6-Methoxy-3-pyridylamine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

5-Amino-2-methoxypyridine Usage And Synthesis

Chemical Properties

yellow-brown or red to very dark red liquid

Uses

5-Amino-2-methoxypyridine is used as a reagent in the synthesis of a novel series of thienopyrimidines as highly potent and selective PI3K inhibitors. 5-Amino-2-methoxypyridine is also used to synthesize EMPA (E521550); a novel high-affinity selective antagonist for the OX2 receptor.

Definition

ChEBI: 6-Methoxypyridin-3-amine is an aminopyridine.

Application

5-Amino-2-methoxypyridine is widely used in drug synthesis, organic synthesis and materials science due to its unique chemical properties and diverse reaction pathways.

Chemical Reactivity

The amino unit in 5-Amino-2-methoxypyridine structure has significant nucleophilicity. It can undergo condensation reactions with acyl chlorides under alkaline conditions to give the corresponding amide derivatives, and it can also undergo condensation reactions with organic carboxylic acids in the presence of condensing agents.

Synthesis

The general procedure for the synthesis of 5-amino-2-methoxypyridine from 5-nitro-2-methoxypyridine was as follows: 67.28 g of 2-methoxy-5-nitropyridine (0.1 mol), 0.50 g of 10% Pd/C were sequentially added to methanol, hydrogen was passed to a pressure of 0.01 MPa, and the reaction was carried out for 62±1.5 hours. Upon completion of the reaction, the reaction solution was cooled to room temperature and filtered to recover the 10% Pd/C catalyst. The filtrate was concentrated under reduced pressure to recover solvent. The residue was extracted twice with 75 g of dichloroethane and the combined extracts were washed once with purified water. Subsequently, the extract was evaporated under reduced pressure to afford a slightly yellow oily liquid 5-amino-2-methoxypyridine 11.69 g. The purity was determined by HPLC to be 97.63% and the yield was 92.03%.

References

[1] Synthesis, 2006, # 19, p. 3316 - 3340
[2] Tetrahedron Letters, 2010, vol. 51, # 5, p. 786 - 789
[3] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 1, p. 302 - 318
[4] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 1, p. 302 - 318
[5] Journal of Heterocyclic Chemistry, 1983, vol. 20, # 1, p. 199 - 203

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