ChemicalBook--->CAS DataBase List--->149520-94-5

149520-94-5

149520-94-5 Structure

149520-94-5 Structure
IdentificationBack Directory
[Name]

1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI)
[CAS]

149520-94-5
[Synonyms]

2-amino-1H-imidazoL
Ethyl 2-AMinoiMidazole-5-carboxylate
Ethyl 2-aMino-1h-iMidazole-4-carboxylate
ETHYL 2-AMINO-1H-IMIDAZOLE-(4)5-CARBOXYLATE
Ethyl 2-amino-1H-imidazole-5-carboxylate 97+%
1H-IMidazole-4-carboxylicacid,2-aMino-,ethylester
2-amino-1H-Imidazole-5-carboxylic acid ethyl ester
1H-IMidazole-5-carboxylic acid, 2-aMino-, ethyl ester
1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI)
ethyl 2-amino-1H-imidazole-5-carboxylate(SALTDATA: FREE)
[Molecular Formula]

C6H9N3O2
[MDL Number]

MFCD09864446
[MOL File]

149520-94-5.mol
[Molecular Weight]

155.15
Chemical PropertiesBack Directory
[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
[form ]

powder
[pka]

12.21±0.10(Predicted)
[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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P280-P302+P352-P304+P340
[HazardClass ]

IRRITANT
[HS Code ]

2922390090
Spectrum DetailBack Directory
[Spectrum Detail]

1H-Imidazole-4-carboxylicacid,2-amino-,ethylester(9CI)(149520-94-5)1HNMR
Hazard InformationBack Directory
[Synthesis]

2-Aminopyrimidine

109-12-6

Ethyl bromopyruvate

70-23-5

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

149520-94-5

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
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