Ethyl pyrazolo[1,5-a]pyrimidine-3-carboxylate

Base Information

• Chemical Name: Ethyl pyrazolo[1,5-a]pyrimidine-3-carboxylate
• CAS No.: 115932-00-8
• Molecular Formula: C9H9N3O2
• Molecular Weight: 191.18700
• Hs Code.: 2933990090
• European Community (EC) Number: 675-307-1
• DSSTox Substance ID: DTXSID00427354
• Wikidata: Q82240016
• ChEMBL ID: CHEMBL4557875
• Mol file: 115932-00-8.mol

Synonyms:ethyl pyrazolo[1,5-a]pyrimidine-3-carboxylate;115932-00-8;Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester;Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid, ethyl ester;ethylpyrazolo[1,5-a]pyrimidine-3-carboxylate;MFCD00847745;F2135-1084;CHEMBL4557875;ETHYL PYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLATE,;SCHEMBL16718858;DTXSID00427354;JEMAMNBFHPIPCR-UHFFFAOYSA-N;STK312787;AKOS000310226;CS-W000737;DS-2908;PB12712;AM807348;SY042783;EN300-82180;A850416;Ethyl pyrazolo[1,5-a]pyrim-idine-3-carboxylate, 99%;Z337709418

Chemical Property of Ethyl pyrazolo[1,5-a]pyrimidine-3-carboxylate

Chemical Property:

• Melting Point: 210-212℃
• PKA: -1.18±0.40(Predicted)
• PSA: 56.49000
• Density: 1.33g/cm3
• LogP: 0.90600
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.5
• 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:

98%min ^*data from raw suppliers

EthylPyrazolo[1,5-a]pyrimidine-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C2N=CC=CN2N=C1

Technology Process of Ethyl pyrazolo[1,5-a]pyrimidine-3-carboxylate

There total 4 articles about Ethyl pyrazolo[1,5-a]pyrimidine-3-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: 85.0%

malonaldehydebis(dimethylacetal) (102-52-3) + ethyl 5-amino-1H-pyrazole-4-carboxylate (1260243-04-6,6994-25-8) → pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester (115932-00-8)

Guidance literature:

With acetic acid; In ethanol; at 90 ℃;

Reference yield:

ethyl 2-cyanoacetate (105-56-6) → pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester (115932-00-8)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic anhydride / 140 °C

2: hydrazine hydrate / ethanol / 3 h / Reflux

3: acetic acid / ethanol / 90 °C

With acetic anhydride; hydrazine hydrate; acetic acid; In ethanol;

Reference yield:

ethyl (ethoxymethylene)cyanoacetate (94-05-3,42466-69-3) → pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester (115932-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrazine hydrate / ethanol; water / -6 - 60 °C / Inert atmosphere; Large scale

2.1: acetic acid / ethanol / 0.83 h / Inert atmosphere; Large scale

2.2: 13.3 h / 73 - 82 °C / Inert atmosphere; Large scale

With hydrazine hydrate; acetic acid; In ethanol; water;

DOI:10.1021/acs.oprd.1c00302

upstream raw materials:

malonaldehydebis(dimethylacetal)

ethyl 5-amino-1H-pyrazole-4-carboxylate

2-cyano-3-ethoxyacrylic acid ethyl ester

ethyl 2-cyanoacetate

Downstream raw materials:

pyrazolo[1,5-a] pyrimidine-3-carboxylic acid

pyrazolo[1,5-a]pyrimidine-3-carbonyl chloride

Refernces

• 1、 -. "Substituted heteroaryl compounds and compositions and uses thereof". Paragraph 0770-0773. . Retrieved 2017/12/02.
• 2、 Maquestiau, A.,Taghret, H.,Eynde, J.-J. vanden. "PREPARATION AND CHARACTERIZATION OF PYRAZOLOPYRIMIDINES". . p. 131 - 136. Retrieved 2007/10/02.