2-Aminopyrimidine

Base Information

• Chemical Name: 2-Aminopyrimidine
• CAS No.: 109-12-6
• Deprecated CAS: 6918-31-6
• Molecular Formula: C4H5N3
• Molecular Weight: 95.1038
• Hs Code.: 29335995
• European Community (EC) Number: 203-648-4
• NSC Number: 1912
• UNII: OB8I17P2G4
• DSSTox Substance ID: DTXSID70870459
• Nikkaji Number: J2.875D
• Wikidata: Q27117919
• Metabolomics Workbench ID: 55936
• ChEMBL ID: CHEMBL88580
• Mol file: 109-12-6.mol

Synonyms:2-aminopyrimidine;aminopyrimidine

Chemical Property of 2-Aminopyrimidine

Chemical Property:

• Appearance/Colour: white to light yellow powder
• Vapor Pressure: 0.00521mmHg at 25°C
• Melting Point: 122-126 °C(lit.)
• Refractive Index: 1.598
• Boiling Point: 275.1 °C at 760 mmHg
• PKA: 3.45(at 20℃)
• Flash Point: 144.5 °C
• PSA: 51.80000
• Density: 1.216 g/cm³
• LogP: 0.64000
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: SOLUBLE
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 95.048347172
• Heavy Atom Count: 7
• Complexity: 48.9

Purity/Quality:

99% ^*data from raw suppliers

2-Aminopyrimidine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrimidines
• Canonical SMILES: C1=CN=C(N=C1)N
• General Description: 2-Aminopyrimidine, also known as pyrimidin-2-amine or 2-Pyrimidinamine, is a versatile heterocyclic compound that serves as a key ligand in coordination chemistry and a building block in medicinal chemistry. It acts as a tridentate ligand in polymeric silver(I) complexes, contributing to the formation of metal-organic frameworks with distinct structural properties. Additionally, it is employed as a nucleophile in the synthesis of heterocyclic aldehydes, demonstrating its utility in organic transformations. In medicinal chemistry, 2-aminopyrimidine derivatives, particularly when linked to 4-aminoquinolines, exhibit potent anti-plasmodial activity against drug-resistant malaria strains, targeting heme detoxification and DNA interactions. Its structural flexibility and functional groups make it valuable in designing bioactive molecules and supramolecular architectures.

Technology Process of 2-Aminopyrimidine

There total 68 articles about 2-Aminopyrimidine 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: 97.0%

Malondialdehyde (542-78-9) → 2-aminopyrimidine (109-12-6)

Guidance literature:

Reference yield: 94.0%

2-bromopyrimidine (4595-60-2) → 2-aminopyrimidine (109-12-6)

Guidance literature:

With copper(I) oxide; potassium carbonate; ammonium hydroxide; N,N-dimethylethylenediamine; In ethylene glycol; at 60 ℃; for 16h; Inert atmosphere;

DOI:10.1039/b916569j

Reference yield: 90.0%

nitro-pyrimidine (79917-54-7) → 2-aminopyrimidine (109-12-6)

Guidance literature:

With triethylamine; In water; at 80 ℃; for 8h; chemoselective reaction; Inert atmosphere; Green chemistry;

DOI:10.1039/c4ra01333f

upstream raw materials:

1,3,3-triethoxypropene

guanidine hydrochloride

2-Amino-4,6-dichloropyrimidine

Propiolaldehyde diethyl acetal

Downstream raw materials:

N-(2-nitrophenyl) pyrimidin-2-amine

N-(2-pyrimidyl)nicotinamide

2-phenethyl-N-pyrimidin-2-yl-succinamic acid

N-pyrimidin-2-yl-undec-10-enamide

Refernces

Catena-poly[[(benzoato-κO)silver(I)]-μ-2-aminopyrimidine- κ²N¹:N³]

10.1107/S0108270104024424

The study focuses on the synthesis and crystal structure analysis of a mononuclear silver(I) complex, specifically bis(2-aminopyridine-xN')(benzoato-xO)silver(I), and its comparison with a polymeric 2-aminopyrimidine-Ag compound. The main objective was to investigate the relationship between the starting materials and the resulting structures, and to understand how different ligands influence the formation of metal-organic compounds. In the experiment, silver(I) oxide (Ag,O) and benzoic acid were used as starting materials to form the silver(I) complex, while 2-aminopyrimidine was employed as a tridentate ligand to obtain the polymeric compound. These chemicals served the purpose of creating distinct structural arrangements in the resulting metal-organic compounds, which were then analyzed for their crystal structures and coordination geometries. The study aimed to contribute to the understanding of inorganic supramolecular chemistry, particularly in the construction of polymeric silver(I) coordination networks, and to explore the potential of these compounds for functional solid materials with controllable properties.

A NOVEL AND VERSATILE SYNTHESIS OF HETEROCYCLIC ALDEHYDES USING DIALKYL 3-OXO-1-ALKENYL-PHOSPHONATES.

10.1016/S0040-4039(00)94151-0

The research focuses on the development of a novel and versatile synthesis method for heterocyclic aldehydes using dialkyl 3-oxo-1-alkenyl-phosphonates. The primary purpose of this study is to explore a three-step transformation process that begins with the preparation of 1,2-epoxy-3-oxoalkyl-phosphonates from 1-alkenyl-phosphonates. These epoxyphosphonates then react with ambident nucleophiles, such as thiourea, 2-amino-pyridine, 2-amino-pyrimidine, and ethyl 2-pyridylacetate, to form dialkyl 1-hetaryl-1-hydroxymethyl-phosphonates. The final step involves mild alkaline treatment to yield the desired heterocyclic aldehydes. The study concludes that α-hydroxyalkyl-phosphonates are significant synthons for carbonyl functions, and the method provides a new route for generating carbonyl units.

2-Aminopyrimidine based 4-aminoquinoline anti-plasmodial agents. Synthesis, biological activity, structure-activity relationship and mode of action studies

10.1016/j.ejmech.2012.03.007

The study investigates the synthesis and biological evaluation of a series of 2-aminopyrimidine based 4-aminoquinoline compounds designed to combat malaria, particularly against drug-resistant strains of Plasmodium falciparum. The researchers synthesized these compounds using a protocol that involved the transformation of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) into 2-aminopyrimidines linked to 4-aminoquinolines. The compounds were evaluated for their in vitro anti-plasmodial activity against both chloroquine-sensitive (CQS) and chloroquine-resistant (CQR) strains of P. falciparum. The study found that some of these compounds, notably 10r, exhibited potent anti-plasmodial activity, with IC50 values significantly lower than that of chloroquine (CQ), especially against the CQR strain. The structure-activity relationship (SAR) analysis revealed that the length and nature of the spacer connecting the pharmacophores, as well as the presence of substituents like nitro groups, influenced the compounds' potency. The mode of action studies indicated that these compounds bind to heme and m-oxo-heme, inhibiting the formation of b-hematin, similar to CQ. Additionally, the compounds showed binding affinity to DNA, particularly AT-rich DNA, suggesting another potential mechanism of action. Molecular docking analysis with Pf DHFR further supported the compounds' ability to interact with this enzyme, which is crucial for the parasite's DNA biosynthesis. Overall, the study highlights the potential of these hybrid compounds as new anti-malarial agents with activity against drug-resistant strains.