4,6-Diamino-5-nitropyrimidine

Base Information

• Chemical Name: 4,6-Diamino-5-nitropyrimidine
• CAS No.: 2164-84-3
• Molecular Formula: C4H5 N5 O2
• Molecular Weight: 155.116
• Hs Code.: 29335990
• European Community (EC) Number: 654-102-0
• NSC Number: 45756,26753
• DSSTox Substance ID: DTXSID40282601
• Wikidata: Q72462964
• Mol file: 2164-84-3.mol

Synonyms:4,6-diamino-5-nitropyrimidine;2164-84-3;5-nitropyrimidine-4,6-diamine;MFCD00023268;NSC 26753;NSC 45756;4,6-Pyrimidinediamine,5-nitro-;NSC26753;nsc 26753;5-nitro-4,6-pyrimidinediamine;SCHEMBL4874040;DTXSID40282601;BCP30402;CS-M1929;NSC45756;BBL005126;NSC-26753;NSC-45756;STL122223;AKOS002336631;GS-5613;SB57809;AC-26678;SY017206;AM20090198;FT-0646014;VU0607196-1;EN300-160558;A815576;AF-399/25039009;W-206661;F3246-0006;5-Nitro-pyrimidine-4,6-diamine pound>>(6-amino-5-nitro-pyrimidin-4-yl)amine

Chemical Property of 4,6-Diamino-5-nitropyrimidine

Chemical Property:

• Vapor Pressure: 1.08E-08mmHg at 25°C
• Melting Point: >250 °C
• Boiling Point: 461.4°Cat760mmHg
• PKA: 2.68±0.10(Predicted)
• Flash Point: 232.8°C
• PSA: 123.64000
• Density: 1.68g/cm³
• LogP: 1.23480
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 155.04432442
• Heavy Atom Count: 11
• Complexity: 147

Purity/Quality:

98% ^*data from raw suppliers

5-nitropyrimidine-4,6-diamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C(C(=N1)N)[N+](=O)[O-])N

Technology Process of 4,6-Diamino-5-nitropyrimidine

There total 5 articles about 4,6-Diamino-5-nitropyrimidine 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: 87.0%

4,6-dichloro-5-nitropyrimidine (4316-93-2) → 4,6-Diamino-5-nitropyrimidine (2164-84-3)

Guidance literature:

With ammonium hydroxide; at 80 ℃; for 7h; Temperature;

Reference yield: 21.7%

4,6-diamino-5-nitrosylpyrimidine (61908-15-4) → 4,6-Diamino-5-nitropyrimidine (2164-84-3) + 5-nitropyrimidine-4,6-diamine 1,3-dioxide (74730-45-3) + 4,6-diamino-5-nitropyrimidin-2-ol (3346-24-5)

Guidance literature:

With dihydrogen peroxide; trifluoroacetic acid; for 12h; Ambient temperature;

Reference yield:

4,6-diaminopyrimidine (2434-56-2) → 4,6-Diamino-5-nitropyrimidine (2164-84-3)

Guidance literature:

With sulfuric acid; nitric acid;

upstream raw materials:

4,6-diaminopyrimidine

4,6-dichloro-5-nitropyrimidine

4-Amino-N,N,6-trimethylpteridin-7-carbonsaeureamid-5,8-dioxid

4,6-diamino-5-nitrosylpyrimidine

Downstream raw materials:

4,5,6-triaminopyrimidine

6-amino-5-nitro-4-(β-D-ribofuranosyl-5-t-butyldiphenylsilyloxy-1,2-dibenzoyl)pyrimidine

(2R,3R,4R,5R)-2-((6-amino-5-nitropyrimidin-4-yl)amino)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate

6-amino-5-nitro-4-[(3',5'-di-O-toluyl-β-D-2'-deoxyribofuranosyl)amino]pyrimidine

Refernces

Efficient synthesis of clitocine via 1,3-N (endo) to N (exo) migration: A revision to Kini's work

10.1055/s-2005-871564

The research aims to develop an efficient synthesis method for clitocine, a compound with significant biological activity, including insecticidal properties and cytostatic effects on leukemia cell lines. The study revisits Kini's previous work and introduces a novel synthetic pathway involving a 1,3-N (endo) to N (exo) migration as a key transformation. The researchers used p-chlorobenzoyl (PCB) as a protecting group to facilitate the solidification of intermediates and minimize epimerization at the final deprotection stage. Key chemicals used in the synthesis include 4,6-diamino-5-nitropyrimidine, 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose, and silica gel for isomerization. The study concludes that the endo-product formed during glycosylation is kinetically favored but isomerizes to the thermodynamically stable exo-product under acid catalysis. The incorporation of the PCB group significantly improves the isolation and purification of intermediates. The final deprotection step using methanol and sodium methoxide yields highly pure clitocine without any column separation, demonstrating a more efficient and practical synthesis route compared to previous methods.