1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI) Chemical Properties

Boiling point:

363.6±34.0 °C(Predicted)

Density 

1.318±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

12.21±0.10(Predicted)

form 

powder

color 

Pale reddish yellow

InChI

InChI=1S/C6H9N3O2/c1-2-11-5(10)4-3-8-6(7)9-4/h3H,2H2,1H3,(H3,7,8,9)

InChIKey

NGJGNTZJCFFZLK-UHFFFAOYSA-N

SMILES

C1(N)NC(C(OCC)=O)=CN=1

Safety Information

HazardClass 

IRRITANT

HS Code 

2922390090

1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI) Usage And Synthesis

Synthesis

The general procedure for the synthesis of ethyl 2-amino-1H-imidazole-5-carboxylate from 2-aminopyrimidine and ethyl 3-bromopyruvate was as follows: to an ethanol solution (20 mL) containing ethyl imidazo[1,2-a]pyrimidine-2-carboxylate and ethyl imidazo[1,2-a]pyrimidine-3-carboxylate (500 mg, 2.62 mmol, 1.0 eq.), hydrazine hydrate ( 180 mg, 2.88 mmol, 1.1 equiv). The reaction mixture was heated and reacted at 75 °C overnight. After completion of the reaction, the reaction mixture was concentrated and the resulting residue was purified by silica gel column chromatography (eluent ratio dichloromethane/methanol = 20/1, v/v) to give ethyl 2-amino-1H-imidazole-4-carboxylate (220 mg, 54% yield) as a yellow solid.

References

[1] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5620 - 5628
[2] Patent: WO2018/11628, 2018, A1. Location in patent: Paragraph 00267

1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI)(149520-94-5)Related Product Information

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