2,5-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol 98% Purity CAS 89852-99-3 Research Grade Dimethyl-Substituted Triazolopyrimidinone Building Block fo

Product Overview

2,5‑Dimethyl‑[1,2,4]triazolo[1,5‑a]pyrimidin‑7‑ol (CAS 89852‑99‑3) is a high‑purity fused heterocyclic compound featuring a triazole ring fused to a pyrimidine ring, with methyl substituents at the 2‑ and 5‑positions and a hydroxyl/keto functionality at the 7‑position. The triazolopyrimidine core is a privileged scaffold in medicinal chemistry, renowned for its ability to participate in hydrogen bonding, π‑stacking, and hydrophobic interactions with biological targets . The presence of methyl groups at the 2‑ and 5‑positions enhances the compound‘s metabolic stability and lipophilicity, potentially improving cell membrane permeability and target engagement . This compound exists in a keto‑enol tautomeric equilibrium, which significantly influences its hydrogen‑bonding capacity, solubility, and derivatization pathways . The electron‑donating methyl substituents increase the electron density of the pyrimidine ring, altering the tautomeric preference and potentially enhancing nucleophilic reactivity at specific positions .

Supplied at ≥98.0% purity as determined by HPLC, this research‑grade reagent is manufactured under strict quality control to ensure batch‑to‑batch consistency. It is intended exclusively for scientific research purposes and is not for human consumption or clinical use.

Synthetic Process

The synthesis of 2,5‑dimethyl‑[1,2,4]triazolo[1,5‑a]pyrimidin‑7‑ol typically involves the cyclization of appropriate 1,2,4‑triazole precursors with β‑dicarbonyl compounds, followed by cyclodehydration to form the fused bicyclic system. A representative synthetic route is described below:

• Step 1 – Preparation of Triazole Precursor: 3,5‑diamino‑1,2,4‑triazole is reacted with acetylacetone or a suitable methyl‑substituted dicarbonyl compound under reflux conditions in acetic acid or ethanol.

• Step 2 – Cyclocondensation: The intermediate undergoes intramolecular cyclocondensation to form the fused triazolopyrimidine ring system. This step may be facilitated by heating in the presence of an acid catalyst such as p‑toluenesulfonic acid or acetic acid.

• Step 3 – Hydroxylation / Keto Formation: The 7‑position is functionalized as a hydroxyl group, existing in tautomeric equilibrium with the keto form. The methyl groups at the 2‑ and 5‑positions are introduced through the choice of appropriate starting materials.

• Step 4 – Purification: The crude product is purified by recrystallization from ethanol, methanol, or a suitable solvent mixture, or by column chromatography on silica gel (eluting with chloroform‑methanol or ethyl acetate‑hexane mixtures).

• Quality Control: The final product is rigorously characterized by melting point determination, HPLC analysis (purity ≥98.0%), ¹H‑NMR, ¹³C‑NMR, and mass spectrometry to confirm structural identity and purity.

Mechanism of Action

As a synthetic intermediate, this compound does not exert a direct pharmacological mechanism of action. However, its chemical structure and the unique combination of the triazolopyrimidine core with methyl substituents make it a versatile precursor for:

• Kinase Inhibitor Synthesis: The triazolopyrimidine core is a privileged scaffold in the design of protein kinase inhibitors, particularly for targets such as PI3K, mTOR, and CDK families. The methyl substituents can modulate binding affinity and selectivity by occupying hydrophobic pockets within kinase active sites . The enhanced electron density of the core due to methyl substitution may also influence π‑stacking interactions with conserved hinge‑region residues.

• Antiviral Research: Derivatives of triazolopyrimidine have been synthesized as inhibitors of viral polymerases and other essential viral proteins. The methyl groups can enhance oral bioavailability and metabolic stability compared to non‑methylated analogs.

• Medicinal Chemistry: Used as a building block for the preparation of diverse compound libraries in drug discovery programs. The keto‑enol tautomerism at the 7‑position enables orthogonal derivatization pathways, including O‑alkylation, C‑alkylation, and condensation reactions, that are not available in 7‑H or fully substituted analogs.

• Agrochemical Research: Fused heterocyclic systems such as triazolopyrimidines are also explored for their potential as herbicides, fungicides, and plant growth regulators.

Packaging & Shipping

• Research quantities: Available in 1g, 5g, 10g, and 25g amber glass vials with PTFE‑lined caps.

• Bulk quantities: Available in 50g, 100g, 500g, and 1kg amber glass bottles.

• Custom packaging: Packaging specifications can be tailored to customer requirements upon request, including special inert‑gas purging and desiccant inclusion.

• Shipping conditions: This product is not classified as dangerous goods under international transport regulations (IMO/IATA). It can be shipped at ambient temperature for routine orders. For long‑distance or high‑temperature routes, refrigerated or insulated packaging is available.

• Storage conditions: Store at 2‑8°C recommended for long‑term storage, protected from light and moisture. For extended storage (>12 months), storage at ‑20°C is recommended.

• Documentation: Each shipment includes a comprehensive Certificate of Analysis (COA) detailing all test results, Material Safety Data Sheet (MSDS), and commercial invoice with full customs declarations for smooth international delivery.

  Parameter	Specification	Details
  Product Name	2,5‑Dimethyl‑[1,2,4]triazolo[1,5‑a]pyrimidin‑7‑ol	Dimethyl‑substituted fused heterocycle
  Synonyms	2,5‑Dimethyl‑[1,2,4]triazolo[1,5‑a]pyrimidin‑7(4H)‑one	—
  CAS Number	89852‑99‑3	89852‑99‑3
  Molecular Formula	C₇H₈N₄O	7 carbons, 8 hydrogens, 4 nitrogens, 1 oxygen
  Molecular Weight	164.16 g/mol	Exact mass: 164.0698
  Appearance	Off‑white to pale yellow crystalline powder	Visual inspection
  Assay (Purity)	≥98.0%	HPLC area normalization
  Melting Point	>250 °C	Capillary method
  Water Content	≤0.5%	Karl Fischer titration
  Residue on Ignition	≤0.1%	Gravimetric analysis
  Heavy Metals	≤20 ppm	ICP‑MS / AAS
  Identification	Conforms to structure	¹H‑NMR, ¹³C‑NMR, HR‑MS
  Residual Solvents	Meets ICH Q3C guidelines	GC headspace analysis
  XlogP	0.8	Computed
  TPSA	61.8 Ų	Computed
  H‑Bond Donors	1	Computed
  H‑Bond Acceptors	2	Computed
  Storage Condition	2‑8°C, protected from light, sealed, dry	Cool, dry place in sealed containers
  Shelf Life	24 months	From date of manufacture
  Packaging	1g, 5g, 10g, 25g, 50g, 100g, 500g, 1kg	Amber glass vials/bottles
  Grade	Research Grade	For laboratory and R&D use
  Signal Word	Warning	—
  Hazard Statements	H302, H315, H319, H335	Harmful if swallowed; skin/eye/respiratory irritant
  Application	Kinase inhibitor synthesis, antiviral research, medicinal chemistry building block	Privileged scaffold for drug discovery