2,4-Diaminopyrimidine

Base Information

• Chemical Name: 2,4-Diaminopyrimidine
• CAS No.: 156-81-0
• Molecular Formula: C4H6N4
• Molecular Weight: 110.118
• Hs Code.: 29335990
• European Community (EC) Number: 205-862-3
• NSC Number: 30856
• UNII: L5ZY0JJP5J
• DSSTox Substance ID: DTXSID70166021
• Nikkaji Number: J79.463E
• Wikipedia: 2,4-Diaminopyrimidine
• Wikidata: Q209196
• Metabolomics Workbench ID: 122976
• ChEMBL ID: CHEMBL1233987
• Mol file: 156-81-0.mol

Synonyms:2,4-diaminopyrimidine

Chemical Property of 2,4-Diaminopyrimidine

Chemical Property:

• Appearance/Colour: light orange crystalline powder
• Vapor Pressure: 1.16E-06mmHg at 25°C
• Melting Point: 143-147 °C(lit.)
• Refractive Index: 1.46-1.466
• Boiling Point: 401.7 °C at 760 mmHg
• PKA: 7.08±0.10(Predicted)
• Flash Point: 225.6 °C
• PSA: 77.82000
• Density: 1.368 g/cm³
• LogP: 0.80340
• Storage Temp.: Refrigerator (+4°C)
• Water Solubility.: 840 g/L (25 ºC)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 110.059246208
• Heavy Atom Count: 8
• Complexity: 74.4

Purity/Quality:

≥98% ^*data from raw suppliers

2,4-Diaminopyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CN=C(N=C1N)N

Technology Process of 2,4-Diaminopyrimidine

There total 20 articles about 2,4-Diaminopyrimidine 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: 48.0%

2-thiocytidine (13233-20-0,13239-97-9) → 2,4-diaminopyrimidine (156-81-0) + cytidine 2′,3′-cyclic monophosphate (50574-59-9) + CYTIDINE (65-46-3)

Guidance literature:

With dihydrogen phosphate; formamide; Heating;

DOI:10.1038/nchem.2664

Reference yield: 27.0%

5-bromopyrimidine-2,4-diamine (1004-01-9) + bis(pinacol)diborane (73183-34-3) → 2,4-diaminopyrimidine (156-81-0) + 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2,4-diamine (944401-61-0)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 115 ℃; for 16h;

Reference yield:

formamide (77287-34-4,77287-35-5,60100-09-6) → pyrimidine-4(3H)-one (51953-18-5,542-27-8) + 2,4-diaminopyrimidine (156-81-0) + guanidine nitrate (113-00-8) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) + 2,6-diaminopyrimidin-4-ol (56-06-4) + urea (57-13-6)

Guidance literature:

With manganese(II) chloride tetrahydrate; In water; at 80 ℃; for 24h; pH=7.57;

DOI:10.1021/acs.biochem.6b00255

upstream raw materials:

2,6-Dichloropyrimidine

6-chloro-pyrimidine-2,4-diyldiamine

2,4-diamino-6-iodopyrimidine

4-chloro-2-ethylsulfanyl-pyrimidine

Downstream raw materials:

5-(4-chloro-phenylazo)-pyrimidine-2,4-diyldiamine

sulfanilic acid-(4-amino-pyrimidin-2-ylamide)

2,4-diaminopyrimidine 3-N-oxide

bis(4-hydroxy-2,6-dimethoxyphenyl)methane

Refernces

Design, synthesis and biological evaluation of novel 2,4-diaminopyrimidine derivatives as potent antitumor agents

10.1039/c9nj02154j

The research aims to develop new therapeutic agents with anticancer activities by designing and synthesizing two series of 2,4-diaminopyrimidine derivatives with triazolopiperazine or 1,4,8-triazaspiro[4.5]decan-3-one scaffolds. The study investigates their antitumor activities against various cancer cell lines and explores their structure-activity relationships (SARs). Key chemicals used include 2,4-dichloropyrimidine, various aromatic aldehydes, and different aliphatic amines for side chain modifications. The most promising compounds, 9k and 13f, showed potent antitumor activities with IC50 values in the micromolar range against A549, HCT-116, PC-3, and MCF-7 cell lines. Mechanistic studies revealed that these compounds inhibited cancer cell proliferation, induced apoptosis, suppressed tumor cell migration, and altered cell cycle distribution. The research concludes that these 2,4-diaminopyrimidine derivatives are promising candidates for further development as anticancer agents, with JAK2 identified as a potential target through molecular docking and enzymatic studies.