5-Aminopyrimidine-2-carbonitrile

Base Information

• Chemical Name: 5-Aminopyrimidine-2-carbonitrile
• CAS No.: 56621-93-3
• Molecular Formula: C5H4N4
• Molecular Weight: 120.11206
• Hs Code.: 2933599090
• European Community (EC) Number: 848-249-1
• DSSTox Substance ID: DTXSID30480851
• Wikidata: Q82315958
• Mol file: 56621-93-3.mol

Synonyms:5-Aminopyrimidine-2-carbonitrile;56621-93-3;5-Amino-2-cyanopyrimidine;5-amino-2-pyrimidinecarbonitrile;5-Aminopyrimidine-2-;2-Pyrimidinecarbonitrile, 5-amino- (9CI);MFCD08234877;2-PYRIMIDINECARBONITRILE, 5-AMINO-;2-cyano-5aminopyrimidine;SCHEMBL254689;5-azanylpyrimidine-2-carbonitrile;DTXSID30480851;NOMODHWDBMCWFQ-UHFFFAOYSA-N;AMY16296;ZB1483;AKOS006287194;AC-2956;PB15970;2-Pyrimidinecarbonitrile,5-amino-(9ci);AS-33712;SY003421;CS-0044715;FT-0646339;A831123

Chemical Property of 5-Aminopyrimidine-2-carbonitrile

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 1.38E-05mmHg at 25°C
• Melting Point: 230-231 °C(Solv: ethanol (64-17-5))
• Refractive Index: 1.6
• Boiling Point: 367.3 °C at 760 mmHg
• PKA: -1.94±0.22(Predicted)
• Flash Point: 175.9 °C
• PSA: 75.59000
• Density: 1.34 g/cm³
• LogP: 0.51168
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 120.043596145
• Heavy Atom Count: 9
• Complexity: 127

Purity/Quality:

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

5-Amino-2-pyrimidinecarbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(C=NC(=N1)C#N)N
• Uses: 5-Amino-2-pyrimidinecarbonitrile is used in the preparation of quinazolines as aurora 2 kinase inhibitors for the treatment of breast and colorectal cancers.

Technology Process of 5-Aminopyrimidine-2-carbonitrile

There total 3 articles about 5-Aminopyrimidine-2-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%

N-(2-cyanopyrimidin-5-yl)-2-methylpropane-2-sulfinamide (1338209-87-2) → 5-aminopyrimidine-2-carbonitrile (56621-93-3)

Guidance literature:

N-(2-cyanopyrimidin-5-yl)-2-methylpropane-2-sulfinamide; With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 0.25h; Inert atmosphere;

With sodium hydrogencarbonate; In 1,4-dioxane; water; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.08.075

Reference yield:

5-chloropyrimidine-2-carbonitrile (38275-56-8) → 5-aminopyrimidine-2-carbonitrile (56621-93-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 15 h / 110 °C / Inert atmosphere

2.1: hydrogenchloride / 1,4-dioxane / 0.25 h / 20 °C / Inert atmosphere

2.2: Inert atmosphere

With hydrogenchloride; palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane;

DOI:10.1016/j.tetlet.2011.08.075

Reference yield:

→ 5-aminopyrimidine-2-carbonitrile (56621-93-3)

Guidance literature:

A: Pyrimidin-Derivat In u. wss. K2CO3;

upstream raw materials:

N-(2-cyanopyrimidin-5-yl)-2-methylpropane-2-sulfinamide

5-chloropyrimidine-2-carbonitrile