1-METHYL-1H-PYRAZOL-4-YLAMINE Chemical Properties

Melting point:

47-50℃

Density 

1.141 g/mL at 25 °C

refractive index 

n20/D1.556

Flash point:

>110 °C

storage temp. 

-20°C

pka

3.70±0.10(Predicted)

form 

liquid

color 

Pale red

Sensitive 

Air Sensitive

Boiling point:

45-80°C/760 mmHg

InChI

InChI=1S/C4H7N3/c1-7-3-4(5)2-6-7/h2-3H,5H2,1H3

InChIKey

HEFHQCFTJGKPMD-UHFFFAOYSA-N

SMILES

N1(C)C=C(N)C=N1

CAS DataBase Reference

69843-13-6

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933199090

1-METHYL-1H-PYRAZOL-4-YLAMINE Usage And Synthesis

Uses

1-Methyl-1H-pyrazole-4-amine is used as an organic and pharmaceutical intermediate.

Synthesis

1-Methyl-4-nitro-1H-pyrazole (1.62 g, 12.7 mmol) was used as the raw material, which was dissolved in methanol (250 mL) and hydrogenated on an H-Cube reactor at 60 bar hydrogen pressure and 70 °C to obtain 1-methyl-1H-pyrazol-4-amine (1.23 g, 99% yield). Subsequently, 1-methyl-1H-pyrazol-4-amine (700 mg, 7.0 mmol), 3-amino-6-bromopyridinecarboxylic acid (1.86 g, 8.5 mmol), PyBop (4.12 g, 8.0 mmol), dichloromethane (30 mL), and diisopropylethylamine (3.8 mL) were added to a 100 mL round-bottomed flask and the reaction mixture was stirred at room temperature for 24 h. The reaction progress was monitored by LCMS. Upon completion of the reaction, the solvent was removed by distillation and the crude product was purified by fast chromatography (eluent: heptane/ethyl acetate). A portion of the product was further purified by reversed-phase HPLC to afford the target compound 317.The product characterization data were as follows:1H NMR (400 MHz, DMSO) δ 10.25 (s, 1H), 8.03 (s, 1H), 7.70 (s, 1H), 7.43 (d, J = 8.7 Hz, 1H), 7.19 (d, J = 8.7 Hz, 1H), 7.02 (br, 2H), 3.81 (s, 3H); MS (ESI) m/z: 296.0/298.0 [M + H]+.

References

[1] Patent: US2011/251176, 2011, A1. Location in patent: Page/Page column 160-161
[2] Patent: WO2015/25197, 2015, A1. Location in patent: Paragraph 00077
[3] Patent: US2015/336982, 2015, A1. Location in patent: Paragraph 0179; 0181
[4] Patent: CN106432246, 2017, A. Location in patent: Paragraph 0453; 0806; 0807; 0808
[5] Patent: WO2015/161830, 2015, A1. Location in patent: Paragraph 00770

1-METHYL-1H-PYRAZOL-4-YLAMINE(69843-13-6)Related Product Information

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