2,4-Diaminopyrimidine-5-carbonitrile

Base Information

• Chemical Name: 2,4-Diaminopyrimidine-5-carbonitrile
• CAS No.: 16462-27-4
• Molecular Formula: C5H5 N5
• Molecular Weight: 135.128
• Hs Code.: 29335990
• European Community (EC) Number: 813-877-7
• NSC Number: 135235
• DSSTox Substance ID: DTXSID60300179
• Wikidata: Q72462753
• Mol file: 16462-27-4.mol

Synonyms:2,4-Diaminopyrimidine-5-carbonitrile;16462-27-4;2,4-Diamino-5-cyanopyrimidine;2,4-Diamino-pyrimidine-5-carbonitrile;2,4-Diamino-5-cyano-pyrimidine;MFCD00085600;5-Pyrimidinecarbonitrile, 2,4-diamino-;2,4-diamino-5-pyrimidine carbonitrile;NSC135235;SCHEMBL263835;DTXSID60300179;AMY11376;STK785133;2,4-diamino-5-pyrimidinecarbonitrile;AKOS004121368;AB03188;GS-5781;NSC 135235;NSC-135235;AC-26680;A3657;CS-0045751;FT-0645894;EN300-170271;W-205938;Z1198150343;4-bromo-1H-pyrazol-3-amine

Chemical Property of 2,4-Diaminopyrimidine-5-carbonitrile

Chemical Property:

• Vapor Pressure: 4.62E-10mmHg at 25°C
• Melting Point: 318 °C (decomp)
• Boiling Point: 498.2°Cat760mmHg
• PKA: 3.93±0.10(Predicted)
• Flash Point: 255.1°C
• PSA: 101.61000
• Density: 1.45g/cm³
• LogP: 0.67508
• Storage Temp.: Refrigerator
• Solubility.: DMF (Slightly, Heated), DMSO (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 135.05449518
• Heavy Atom Count: 10
• Complexity: 159

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,4-Diaminopyrimidine-5-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=NC(=N1)N)N)C#N
• Uses: 2,4-Diaminopyrimidine-5-carbonitrile is used as an intermediate for the preparation of medicines and agrochemicals (1). Intermediate for the preparation of medicines and agrochemicals.

Technology Process of 2,4-Diaminopyrimidine-5-carbonitrile

There total 9 articles about 2,4-Diaminopyrimidine-5-carbonitrile 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: 79.0%

guanidine hydrochloride (50-01-1) + Ethoxymethylenemalononitrile (123-06-8) → 2,4-diamino-pyrimidine-5-carbonitrile (16462-27-4)

Guidance literature:

guanidine hydrochloride; With sodium ethanolate; for 0.166667 - 0.25h; Reflux;

Ethoxymethylenemalononitrile; at 20 ℃; for 8h;

DOI:10.1016/j.bmcl.2012.02.019

Reference yield: 76.0%

4-amino-2-chloropyrimidine-5-carbonitrile (94741-69-2) → 2,4-diamino-pyrimidine-5-carbonitrile (16462-27-4)

Guidance literature:

With ammonia; at 60 ℃; for 0.333333h;

Reference yield: 71.0%

guanidine nitrate (506-93-4) + Ethoxymethylenemalononitrile (123-06-8) → 2,4-diamino-pyrimidine-5-carbonitrile (16462-27-4)

Guidance literature:

With sodium ethanolate; In ethanol; at 5 ℃; for 8h;

upstream raw materials:

4-amino-2-(ethylthio)pyrimidine-5-carbonitrile

guanidine nitrate

Ethoxymethylenemalononitrile

4-amino-2-chloropyrimidine-5-carbonitrile

Downstream raw materials:

5-(aminomethyl)pyrimidine-2,4-diamine

2,4-Diamino-5-carbamoyl-pyrimidin

2-(4-(2-(pyrrolidin-1-yl)ethoxy)phenylamino)-4-aminopyrimidine-5-carbonitrile

5-((4-methoxyphenylamino)methyl)pyrimidine-2,4-diamine

Refernces

• 1、 He, Haifeng,Xia, Hongying,Xia, Qin,Ren, Yanliang,He, Hongwu. "Design and optimization of N-acylhydrazone pyrimidine derivatives as E. coli PDHc E1 inhibitors: Structure-activity relationship analysis, biological evaluation and molecular docking study". . p. 5652 - 5661. Retrieved 2017/10/09.
• 2、 Karoli, Tomislav,Mamidyala, Sreeman K.,Zuegg, Johannes,Fry, Scott R.,Tee, Ernest H.L.,Bradford, Tanya A.,Madala, Praveen K.,Huang, Johnny X.,Ramu, Soumya,Butler, Mark S.,Cooper, Matthew A.. "Structure aided design of chimeric antibiotics". supporting information; experimental part. p. 2428 - 2433. Retrieved 2012/05/19.