64951-06-0

Basic information

• Product Name: IMIDAZO[1,2-A]PYRIMIDINE-2-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: ETHYL IMIDAZO[1,2-A]PYRIMIDINE-2-CARBOXYLATE;IMIDAZO[1,2-A]PYRIMIDINE-2-CARBOXYLIC ACID ETHYL ESTER;Ethy imidazol[1,2-a]pyrimidine-2-carboxylate;Ethyl iMidazol[1,2-a]pyriMidine-2-carboxylate;Ethyl Imidazo[1,2-A]Pyrimidine-2-Carboxylate(WXC03684)
• CAS NO: 64951-06-0
• Molecular Formula: C9H9N3O2
• Molecular Weight: 191.19
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 64951-06-0.mol

Chemical Properties

• Melting Point: 170-172°
• Appearance: /
• Density: 1.332g/cm³
• Refractive Index: 1.629
• Storage Temp.: 2-8°C
• PKA: 1.98±0.30(Predicted)
• CAS DataBase Reference: IMIDAZO[1,2-A]PYRIMIDINE-2-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: IMIDAZO[1,2-A]PYRIMIDINE-2-CARBOXYLIC ACID ETHYL ESTER(64951-06-0)
• EPA Substance Registry System: IMIDAZO[1,2-A]PYRIMIDINE-2-CARBOXYLIC ACID ETHYL ESTER(64951-06-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 64951-06-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Imidazo[1,2-a]pyrimidine-2-carboxylic acid ethyl ester is used as a key intermediate in the synthesis of various pharmaceuticals for its potential biological activities. It serves as a building block in the development of new drugs, particularly those with antifungal and anticancer properties, contributing to the advancement of treatments for a range of diseases.
Used in Agrochemical Industry:
In the agrochemical sector, Imidazo[1,2-a]pyrimidine-2-carboxylic acid ethyl ester is employed as a precursor in the production of agrochemicals. Its incorporation aids in the creation of compounds that can protect crops from fungal infections, thereby enhancing agricultural productivity and crop yield.
Used in Chemical Research:
Imidazo[1,2-a]pyrimidine-2-carboxylic acid ethyl ester is also utilized in chemical research as a model compound for studying the properties and reactions of heterocyclic compounds. Its unique structure allows scientists to explore new chemical pathways and mechanisms, potentially leading to the discovery of novel applications and compounds.

InChI:InChI=1/C9H9N3O2/c1-2-14-8(13)7-6-12-5-3-4-10-9(12)11-7/h3-6H,2H2,1H3

Upstream product

• 109-12-6 2-aminopyrimidine 
• 70-23-5 ethyl Bromopyruvate 
• 617-35-6 2-oxo-propionic acid ethyl ester 

Downstream Products

• 134044-63-6 3-Bromo-imidazo[1,2-a]pyrimidine-2-carboxylic acid ethyl ester 
• 149520-94-5 2-amino-1H-imidazole-4-carboxylic acid ethyl ester 
• 860612-52-8 ethyl 3-chloroimidazo[1,2-a]pyrimidine-2-carboxylate 

Relevant articles and documents

TRICYCLIC PESTICIDAL COMPOUNDS

The invention relates to compounds of formula (I), wherein the variables are as defined in the specification. It also relates to the use of compounds of formula (I) as an agrochemical pesticide; to pesticidal mixtures comprising compounds of formula (I); and to agrochemical or veterinary compositions comprising compounds of formula (I). Other objects are seed comprising compounds of formula (I); and methods for controlling invertebrate pests, infestation, or infection by invertebrate pests by application of compounds of formula (I).

New geldanamycin derivatives with anti Hsp properties by mutasynthesis

Mutasynthetic supplementation of the AHBA blocked mutant strain of S. hygroscopicus, the geldanamycin producer, with 21 aromatic and heteroaromatic amino acids provided new nonquinoid geldanamycin derivatives. Large scale (5 L) fermentation provided four new derivatives in sufficient quantity for full structural characterisation. Among these, the first thiophene derivative of reblastatin showed strong antiproliferative activity towards several human cancer cell lines. Additionally, inhibitory effects on human heat shock protein Hsp90α and bacterial heat shock protein from H. pylori HpHtpG were observed, revealing strong displacement properties for labelled ATP and demonstrating that the ATP-binding site of Hsps is the target site for the new geldanamycin derivatives.

Efficient Access to Imidazo[1,2- a] pyridines/pyrazines/pyrimidines via Catalyst-Free Annulation Reaction under Microwave Irradiation in Green Solvent

An expeditious catalyst-free heteroannulation reaction for imidazo[1,2-a]pyridines/pyrimidines/pyrazines was developed in green solvent under microwave irradiation. Using H2O-IPA as the reaction medium, various substituted 2-aminopyridines/pyra

THERAPEUTIC INHIBITORY COMPOUNDS

Provided herein are heterocyclic derivative compounds and pharmaceutical compositions comprising said compounds that are useful for inhibiting plasma kallikrein. Furthermore, the subject compounds and compositions are useful for the treatment of diseases wherein the inhibition of plasma kallikrein inhibition has been implicated, such as angioedema and the like.

Discovery of 6-(Aminomethyl)-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2- α]pyrimidine-2-carboxamides as potent, selective dipeptidyl peptidase-4 (DPP4) inhibitors

Continued structure-activity relationship (SAR) exploration within our previously disclosed azolopyrimidine containing dipeptidyl peptidase-4 (DPP4) inhibitors led us to focus on an imidazolopyrimidine series in particular. Further study revealed that by replacing the aryl substitution on the imidazole ring with a more polar carboxylic ester or amide, these compounds displayed not only increased DPP4 binding activity but also significantly reduced human ether-à-go-go related gene (hERG) and sodium channel inhibitory activities. Additional incremental adjustment of polarity led to permeable molecules which exhibited favorable pharmacokinetic (PK) profiles in preclinical animal species. The active site binding mode of these compounds was determined by X-ray crystallography as exemplified by amide 24c. A subsequent lead molecule from this series, (+)-6-(aminomethyl)-5-(2,4-dichlorophenyl)-N-(1-ethyl-1H- pyrazol-5-yl)-7-methylimidazo[1,2-a]pyrimidine-2-carboxamide (24s), emerged as a potent, selective DPP4 inhibitor that displayed excellent PK profiles and in vivo efficacy in ob/ob mice.

AZOLOPYRIMIDINE-BASED INHIBITORS OF DIPEPTIDYL PEPTIDASE IV AND METHODS

Compounds are provided having the formula (I): Formula (I) wherein R, X, Y, A and n are as defined herein.

Research on heterocyclic compounds. XXXII. Synthesis and cyclooxygenase-independent antiinflammatory and analgesic activity of imidazopyrimidine derivatives

The synthesis of a group of imidazopyrimidine-2-carboxylic esters, acids and amides is described.The structures of the new compounds are supported by 1H- and 13C-NMR spectra.These compounds were tested in vivo for their antiinflammatory and analgesic activities as well as for their ulcerogenic action.The ester 5b, the acid 6c and the amide 7a showed antiinflammatory action in the rat paw edema (ca. 1/3 x indomethacin), while almost all compounds displayed significant analgesic activity in the acetic acid writhing test, particularly the 5-chloro-7-methyl derivatives 5a, 6a and 7a (ca 1/5 x indomethacin).All new compounds were found to be lacking in inhibitory activity on cyclooxygenase in vitro. imidazopyrimidines / antiinflammatory activity / analgesic activity / ulcerogenic activity / cyclooxygenase inhibition

Synthesis and antibacterial activity of some imidazo[1,2-a[pyrimidine derivatives

A series of 75 imidazo[1,2-a]pyrimidine derivatives were synthesized. The 'in vitro' antibacterial activity of these compounds and their corresponding α-bromoketones against a variety of gram (+), gram (-) bacteria and Mycobacterium species is reported. Some of the prepared derivatives exhibited potent antimicrobial activity.

Antifungal activity in vitro of some imidazopyrimidine derivatives

In regard to fungicidal activity of imidazole ring found in chemical compounds such as econazole, a series of 42 diversely substituted imidazopyrimidines was synthetized and examined for its antifungal activity in several species.