N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine
[CAS# 152460-10-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound
• Name: N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine
• Synonyms: 4-Methyl-3-[4-(3-pyridyl)pyrimidin-2-ylamino]aniline; 4-Methyl-N'-[4-(pyridin-3-yl)pyrimidin-2-yl]benzene-1,3-diamine
• Molecular Formula: C₁₆H₁₅N₅
• Molecular Weight: 277.32
• CAS Registry Number: 152460-10-1
• EC Number: 604-859-8
• SMILES: CC1=C(C=C(C=C1)N)NC2=NC=CC(=N2)C3=CN=CC=C3

Properties

• Density: 1.3$+/-$0.1 g/cm³ Calc.^*
• Melting point: 143 - 147 $degree$C (Expl.)
• Boiling point: 537.3$+/-$60.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 278.8$+/-$32.9 $degree$C (Calc.)^*
• Index of refraction: 1.688 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P264-P264+P265-P270-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P332+P317-P337+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

N-(5-Amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine is a heterocyclic compound that combines a substituted pyrimidine ring with an aniline and a pyridyl moiety. Pyrimidine derivatives have been extensively studied in medicinal chemistry due to their presence in nucleic acids and their capacity to interact with enzymes, receptors, and other biological macromolecules. The incorporation of an amino-substituted phenyl group and a pyridyl group provides additional hydrogen-bonding and π–π stacking capabilities, which enhance the molecule’s potential for biological activity and its utility as a synthetic intermediate. Structurally, the molecule consists of a 2-pyrimidineamine core substituted at the 4-position with a 3-pyridyl group and at the exocyclic nitrogen with a 5-amino-2-methylphenyl moiety. The pyrimidine ring serves as a planar heteroaromatic scaffold capable of engaging in hydrogen bonding and π–π interactions, making it a privileged structure in drug discovery. The amino group on the phenyl ring contributes additional hydrogen-bonding potential, while the methyl group modifies steric and electronic properties, influencing solubility and receptor binding. The pyridyl group adds another aromatic heterocycle that can participate in π–π stacking and coordinate with metal ions in enzyme active sites. Synthetically, compounds of this type are generally prepared through nucleophilic aromatic substitution or palladium-catalyzed cross-coupling reactions. The 2,4-dihalopyrimidine intermediates are typically functionalized with aniline derivatives to introduce the exocyclic N-substituted phenyl group, followed by coupling of the pyridyl moiety at the 4-position. These synthetic approaches allow for regioselective substitution and maintain the structural integrity of the heterocyclic core, providing access to high-purity derivatives suitable for chemical and biological studies. The compound’s design makes it suitable for exploration in pharmaceutical research, particularly as a potential inhibitor of enzymes such as kinases, polymerases, or other proteins involved in cellular signaling pathways. Pyrimidine-based scaffolds are widely recognized for their ability to bind in ATP-binding pockets of kinases or nucleotide-binding sites of enzymes, and the presence of additional hydrogen-bond donors and acceptors enhances selectivity and affinity. The combination of planar heterocycles and substituents allows medicinal chemists to optimize interactions with protein targets, improve solubility, and modulate pharmacokinetic properties. Beyond direct biological activity, N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine serves as a versatile intermediate for further chemical modification. The amino group on the phenyl ring can undergo acylation, sulfonylation, or reductive transformations, while the pyrimidine and pyridyl rings provide handles for further cross-coupling, halogenation, or functionalization. This versatility makes the compound valuable in the synthesis of more complex heterocyclic structures and in the development of chemical libraries for screening programs. Overall, N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-pyrimidineamine exemplifies a functionalized heterocyclic molecule that combines the chemical and pharmacological advantages of pyrimidine, aniline, and pyridyl moieties. Its structural features provide opportunities for hydrogen bonding, π–π interactions, and further derivatization, making it a useful scaffold in medicinal chemistry, synthetic organic chemistry, and drug discovery research.

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