Ethyl imidazo[1,2-a]pyrimidine-2-carboxylate

Base Information

• Chemical Name: Ethyl imidazo[1,2-a]pyrimidine-2-carboxylate
• CAS No.: 64951-06-0
• Molecular Formula: C₉H₉N₃O₂
• Molecular Weight: 191.189
• Hs Code.: 2933990090
• European Community (EC) Number: 673-856-1
• DSSTox Substance ID: DTXSID60374754
• Nikkaji Number: J374.505H
• Wikidata: Q72475458
• ChEMBL ID: CHEMBL1581220
• Mol file: 64951-06-0.mol

Synonyms:ethyl imidazo[1,2-a]pyrimidine-2-carboxylate;64951-06-0;Ethy imidazol[1,2-a]pyrimidine-2-carboxylate;Imidazo[1,2-a]pyrimidine-2-carboxylic acid ethyl ester;MFCD02186164;1613037-69-6;rel-(4R,5R)-5-(Prop-2-yn-1-yloxy)-1,2-dithian-4-ol;SMR000126017;MLS000540959;SCHEMBL1407731;CHEMBL1581220;DTXSID60374754;SORASSFGEFQWIH-UHFFFAOYSA-N;HMS2326P15;BBL021337;STK894049;AKOS005070254;AB11553;CS-W002930;AC-23608;SY014179;AM20100587;FT-0646431;EN300-76066;ethyl imidazo[1,2-a]py-rimidine-2-carboxylate;3R-0666;A867784;W-60392;J-521255;imidazo[1,2-a]pyrimidine-2-carboxylic acid ethylester;Z666291320

Chemical Property of Ethyl imidazo[1,2-a]pyrimidine-2-carboxylate

Chemical Property:

• Melting Point: 170-172°
• Refractive Index: 1.629
• PKA: 1.98±0.30(Predicted)
• PSA: 56.49000
• Density: 1.332g/cm³
• LogP: 0.90600
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 191.069476538
• Heavy Atom Count: 14
• Complexity: 222

Purity/Quality:

97% ^*data from raw suppliers

Ethyl imidazo[1,2-a]pyrimidine-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN2C=CC=NC2=N1

Technology Process of Ethyl imidazo[1,2-a]pyrimidine-2-carboxylate

There total 4 articles about Ethyl imidazo[1,2-a]pyrimidine-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

2-aminopyrimidine (109-12-6) + ethyl Bromopyruvate (70-23-5) → ethyl imidazo<1,2-a>pyrimidine-2-carboxylate (64951-06-0)

Guidance literature:

In water; isopropyl alcohol; at 75 ℃; Microwave irradiation; Green chemistry;

DOI:10.1021/acscombsci.7b00173

Reference yield: 30.0%

2-aminopyrimidine (109-12-6) + ethyl Bromopyruvate (70-23-5) → ethyl imidazo<1,2-a>pyrimidine-3-carboxylate (64951-07-1) + ethyl imidazo<1,2-a>pyrimidine-2-carboxylate (64951-06-0)

Guidance literature:

In ethanol; at 75 ℃; for 16h;

Reference yield:

2-oxo-propionic acid ethyl ester (617-35-6) → ethyl imidazo<1,2-a>pyrimidine-2-carboxylate (64951-06-0)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / dioxane; diethyl ether / 1 h

2: 1,2-dimethoxy-ethane / 48 h / Heating

With bromine; In 1,4-dioxane; 1,2-dimethoxyethane; diethyl ether;

DOI:10.1248/cpb.40.1170

upstream raw materials:

2-aminopyrimidine

ethyl Bromopyruvate

2-oxo-propionic acid ethyl ester

Downstream raw materials:

3-Bromo-imidazo[1,2-a]pyrimidine-2-carboxylic acid ethyl ester

2-amino-1H-imidazole-4-carboxylic acid ethyl ester

ethyl 3-chloroimidazo[1,2-a]pyrimidine-2-carboxylate