Section
| HS Code | 788008 |
| Product Name | 2,4,6,8-Tetrahydroxypyrimido[5,4-d]pyrimidine |
| Iupac Name | pyrimido[5,4-d]pyrimidine-2,4,6,8-tetrol |
| Cas Number | 67107-89-3 |
| Molecular Formula | C6H4N4O4 |
| Molecular Weight | 196.12 g/mol |
| Exact Mass | 196.0233 Da |
| Canonical Smiles | c12nc(O)nc(O)c1c(O)nc(O)n2 |
| Topological Polar Surface Area | 132.48 Ų |
| Physical State | Solid |
| Appearance | Off-white to pale yellow powder |
| Storage Condition | Store at room temperature, protected from light and moisture |
As an accredited 2,4,6,8-Tetrahydroxypyrimido [5,4-d] Pyrimidine factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | Supplied as 1 g in a sealed amber glass vial with a secure screw cap and clearly marked chemical-resistant label. |
| Container Loading (20′ FCL) | 2,4,6,8-Tetrahydroxypyrimido[5,4-d]pyrimidine loaded in a clean, dry 20-foot FCL container, secured and protected from moisture and contamination. |
| Shipping | 2,4,6,8-Tetrahydroxypyrimido[5,4-d]pyrimidine should be shipped in sealed, labeled, moisture-resistant containers with secondary containment, protected from heat, light, and physical damage. Use UN-certified packaging where required and verify hazard classification, labels, and documentation against the current SDS and applicable transport regulations. Do not ship as non-hazardous unless supported by an SDS/transport review. |
| Storage | Store in a cool, dry, well-ventilated area away from heat, ignition sources, and direct sunlight. Keep the container tightly closed, clearly labeled, and protected from moisture. Separate from strong oxidizing agents, acids, and bases. Use appropriate secondary containment and follow the supplier’s safety data sheet. Wear suitable personal protective equipment when handling. |
| Shelf Life | Shelf life: Stable under recommended storage conditions; store cool, dry, protected from light and moisture, and refer to supplier expiry. |
In dipyridamole-type antiplatelet API manufacturing, 2,4,6,8-tetrahydroxypyrimido[5,4-d]pyrimidine serves as the chlorination substrate for the pyrimido[5,4-d]pyrimidine core. The tetraol is suspended in phosphorus oxychloride at 6–10 molar equivalents per hydroxyl-bearing ring. The slurry is heated to 105–115 °C under anhydrous nitrogen in a glass-lined reactor equipped with a reflux condenser and a caustic scrubber for evolved HCl. The exotherm is managed by staged solid addition and jacket cooling; N,N-dimethylaniline is charged at 0.05–0.10 mol per mole substrate to accelerate chloride transfer and reduce tar formation. The conversion replaces all four hydroxyl positions with chloride, yielding 2,4,6,8-tetrachloropyrimido[5,4-d]pyrimidine. Residual phosphorus oxychloride is distilled under reduced pressure, and the concentrated mass is quenched into ice water maintained below 5 °C. The crude solid is filtered on a pressure nutsche and washed with cold deionized water to remove phosphate by-products. The dried intermediate is then reacted sequentially with diethanolamine and piperidine; process literature reports molar charges of 1.0 mol tetrachloride to 4.0–4.5 mol diethanolamine and 2.0–2.2 mol piperidine. Compliance in this downstream segment is governed by ICH Q7 for API starting materials, with phosphorus-containing impurities monitored by gas chromatography and residual solvent limits aligned with Ph. Eur. 2.4.24. The tetraol must be dried to <1.0% moisture before chlorination because residual water hydrolyzes POCl3 and generates uncontrolled HCl vapour. Published data for exact batch yields in cGMP campaigns is limited; laboratory chlorination yields from 68% to 82% are documented after recrystallization from toluene or dichloromethane.
Evaluation of char formation in polyolefin systems places the tetrahydroxy compound alongside ammonium polyphosphate and melamine as a phosphorus-nitrogen intumescent package. Counter-rotating twin-screw compounding with L/D 40:1 and barrel temperatures between 165 °C and 190 °C is used to disperse the finely milled solid at 15–25 wt% into polypropylene or polyethylene. The ammonium polyphosphate charge is maintained at 20–28 wt% and melamine at 8–12 wt%. The ratio between APP and the tetraol is the critical threshold; a deviation of ±2 wt% can shift UL 94 performance from V-0 to V-2 at 3.2 mm. Processing is constrained by the dehydration threshold of the tetraol near 200–210 °C; excursions above this range generate water vapor inside the melt, causing screw slippage and surface defects. All solid ingredients are pre-dried to <0.5% moisture before extrusion. Flammability is assessed by cone calorimetry according to ISO 5660-1 at 50 kW/m² and limiting oxygen index by ASTM D2863. The char residue obtained at 600 °C in thermogravimetric analysis shows a cellular structure typical of polyol-phosphate intumescent systems. Published data for this specific configuration is limited; the exact expansion ratio depends on melt viscosity, mold venting, and the particle size distribution of the solid additive.
Acid copper electroplating screening in high-acid low-copper damascene electrolytes evaluates the tetraol as a polar leveler candidate. The base electrolyte contains CuSO4·5H2O at 40–60 g/L, H2SO4 at 180–220 g/L, and chloride at 30–60 mg/L. The compound is pre-dissolved as a 1–5 g/L stock solution and dosed into the working bath at 5–30 mg/L. Hull cell tests in a 267 mL cell at 2 A for 5 min map deposit appearance across the current density gradient. Cyclic voltammetry on a platinum rotating disc electrode at 1000–4000 rpm and 10–50 mV/s scan rate quantifies cathodic suppression. The heteroatom-rich molecule adsorbs preferentially on high-electric-field protrusions and reduces local deposition rate. Filling of 5–20 µm trenches is inspected by cross-sectional scanning electron microscopy after copper plating. Bath temperature must remain below 35 °C; above this limit additive decomposition accelerates and sulfur-bearing breakdown products accumulate. Areal surface roughness after chemical mechanical polishing is characterized by ISO 25178-2. Published data for this specific configuration is limited; current adoption is confined to laboratory screening rather than high-volume printed circuit board production.
Solvothermal coordination polymer synthesis uses the tetrahydroxy compound as a rigid polydentate O,N-donor linker for metal-organic framework screening. The ligand is combined with ZrCl4 or FeCl3·6H2O at metal-to-ligand molar ratios of 1:0.25 to 1:0.5 in DMF/water or DMF/acetic acid media at 100–130 °C for 18–36 h. After cooling, the precipitate is washed with DMF and methanol and extracted in a Soxhlet apparatus for 12 h before activation at 120 °C under vacuum. Nitrogen adsorption is measured according to ISO 9277:2010; the resulting BET surface areas are frequently below 300 m²/g because the hydroxyl-rich network partially collapses upon solvent removal. Aqueous metal uptake is evaluated with 10–50 mg/L Cu(II) and Pb(II) solutions at pH 4.5–5.5, with residual ion concentration measured by inductively coupled plasma optical emission spectroscopy. The material is incompatible with strongly alkaline streams above pH 8, where progressive deprotonation and oxidative ring degradation reduce cyclic reuse. Published data for this specific configuration is limited; the performance is inferred from analogous polyhydroxy heterocyclic linkers rather than from an established framework database.
Resorcinol-free adhesion promoter development for polyester and polyamide tire cord evaluates the tetraol as a methylene acceptor in aqueous resin-latex formulations. The compound replaces resorcinol at 0.5–1.0 molar substitution relative to formaldehyde, while the formaldehyde-to-phenolic equivalent molar ratio is maintained between 1.6 and 2.2. The resin maturation step proceeds at 20–25 °C for 6–12 h at pH 9.0–10.5, followed by the addition of vinylpyridine–styrene–butadiene latex at 15–20 wt% solids. The cord is dipped, dried at 120–150 °C, and cured at 210–235 °C in forced-air ovens. Adhesion between rubber and the treated cord is measured by the H-test procedure described in ISO 36:2017. The critical boundary is the final dip pH; below pH 8.5 the resin condensation slows and adhesion force drops, while above pH 11 latex stability is compromised. Published data for this specific configuration is limited; the compound is not compatible with amine-catalyzed epoxy cord activators because the tetraol can form hydrogen-bonded complexes that retard the epoxy cure.
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2,4,6,8-Tetrahydroxypyrimido[5,4-d]pyrimidine is a fused bicyclic heterocycle with molecular formula C6H4N4O4 and molar mass 196.12 g mol⁻¹. The structural notation indicates four hydroxy groups at positions 2, 4, 6, and 8 of the pyrimido[5,4-d]pyrimidine core; in the solid state and in many neutral aqueous systems, the compound is more accurately represented as the tetraoxo tautomer, pyrimido[5,4-d]pyrimidine-2,4,6,8(1H,3H,5H,7H)-tetraone. The calculated elemental composition is C 36.74%, H 2.06%, N 28.56%, O 32.64%. Because no harmonised pharmacopoeial or ISO monograph exists for this specific intermediate, the supplier certificate of analysis remains the controlling specification; incoming quality control should verify identity by infrared spectroscopy, ¹H/¹³C nuclear magnetic resonance, and liquid chromatography–mass spectrometry against a qualified reference standard.
Commercial grades are typically research-grade or fine-chemical intermediates rather than formulated end-use products. Ordering codes and lot sizes are supplier-specific; no unified product model numbering system applies. The compound should be specified by full IUPAC name, chemical registry number when assigned by the supplier or regulatory inventory, molecular formula, and intended tautomeric form, because the tetrahydroxy and tetraoxo notations may be used interchangeably but can imply different reference analytical spectra.
The presence of four hydroxy groups on ring carbons adjacent to nitrogen creates a lactam–lactim equilibrium. In pyrimidine chemistry, the lactam oxygen generally dominates under ambient crystalline packing conditions; therefore, a Fourier-transform infrared spectrum of a solid batch may show strong carbonyl stretching bands near 1680–1720 cm⁻¹ rather than the broad O–H envelope expected from the literal tetrahydroxy structure. This analytical discrepancy is not a batch failure; it is a structural descriptor issue. A certificate of analysis that references the tetraoxo tautomer by infrared and ¹³C NMR should be treated as equivalent only when the same reference standard is used. Liquid chromatography–mass spectrometry in negative electrospray ionisation may be complicated by the formation of multiple ionic species; method robustness therefore requires buffered mobile-phase conditions. The pH of the sample diluent is a critical process variable: at alkaline pH, ionisation of the hydroxy or lactam NH sites can shift retention, alter ultraviolet absorbance, and change peak shape on reverse-phase C18 columns. Published data for the exact pKa values of this compound are limited, so pH excursions should be treated as an uncharacterised risk and controlled by preparation of fresh sample diluents.
Moisture and residual solvent control are more material-specific than the molecular structure alone would suggest. The compound is a polyfunctional hydrogen-bond donor/acceptor; even when the tetraoxo tautomer dominates, the crystal lattice can retain water or polar solvents such as dimethylformamide or dimethylsulfoxide. Water content by Karl Fischer titration should be included in release testing. Water determination by ISO 760:1978 should be below the supplier’s stated limit; sulfated ash by Ph. Eur. 2.4.14 controls non-volatile inorganics. High-performance liquid chromatography purity is usually reported as area% at UV 254 nm; however, area% is not an absolute purity value unless a certified reference standard and an impurity response factor are established. Storage is recommended under dry conditions; exposure to relative humidity above 60% should be avoided unless hygroscopicity data are available for the specific crystalline batch. The material should not be combined with strong oxidising agents in dry powder blending because the heterocyclic framework may be oxidised, and the resulting exotherm is uncharacterised.
| Parameter | Reference or basis | Representative quality-control approach |
|---|---|---|
| Molecular formula | C6H4N4O4 | Calculated from structure |
| Molar mass | 196.12 g mol⁻¹ | Calculated from IUPAC atomic weights |
| Assay | Supplier certificate of analysis | HPLC area% at 254 nm, C18 column 150 mm × 4.6 mm, 5 μm; countercheck by qNMR |
| Water content | ISO 760:1978 | Karl Fischer coulometric titration |
| Sulfated ash | Ph. Eur. 2.4.14 | Ignition at 600 °C with sulfuric acid |
| Residual solvents | ICH Q3C or supplier method | Headspace GC-FID |
Because the compound lacks a harmonised monograph, the release-testing framework is a risk-based internal control rather than a regulatory compliance checklist. The identity test should include both infrared and ¹H NMR; relying on retention time alone in HPLC is insufficient to distinguish the enol and keto tautomers. For infrared spectroscopy, the carbonyl region between 1680 cm⁻¹ and 1720 cm⁻¹ is the most informative zone; for NMR, the presence or absence of exchangeable proton signals in DMSO-d6 is batch-specific.
Differences from the tetraoxo, tetraamino, and parent pyrimido[5,4-d]pyrimidine derivatives are most relevant in medicinal chemistry and in ligand-design applications. The tetrahydroxy/tetraoxo system offers four potential coordination or hydrogen-bonding positions around a planar bicyclic scaffold; the tetraamino analogue replaces the oxygen-centred donors with nitrogen-centred donors, shifting the electronic character from electron-poor to electron-rich. The parent pyrimido[5,4-d]pyrimidine lacks the hydroxo substituents and therefore has less capacity for intermolecular hydrogen bonding. The 2,4,6,8-tetrahydroxy nomenclature should not be confused with 2,4,6,8-tetranitropyrimido[5,4-d]pyrimidine, which contains nitro groups and is subject to energetic-material handling requirements.
| Compound | Key substituents | Typical consequence | Relevant control |
|---|---|---|---|
| 2,4,6,8-Tetrahydroxypyrimido[5,4-d]pyrimidine | OH/enol to carbonyl lactams | High hydrogen-bond density, potential tautomeric variability | IR, ¹H NMR, water content |
| 2,4,6,8-Tetraoxopyrimido[5,4-d]pyrimidine | Carbonyl at same positions | Same molecular formula; different reference spectrum | Solid-state IR, XRPD |
| 2,4,6,8-Tetraaminopyrimido[5,4-d]pyrimidine | NH₂ donors | Basic centres, different ionisation and metal-binding profile | LC-MS, pKa characterisation |
| 2,4,6,8-Tetranitropyrimido[5,4-d]pyrimidine | NO₂ groups | Potential energetic sensitivity | DSC, BAM impact/friction testing |
When substituting the tetrahydroxy compound into a synthetic route that previously used the tetraoxo form, the batch record should compare molar charge on an equivalent basis of C6H4N4O4; both notations have the same molar mass, so the charge weight is unaffected. However, the physical form may differ in bulk density and flow. Published data for bulk density of this specific configuration is limited; therefore, use of volumetric feeding equipment without calibration can introduce dosing error. The difference in tautomer identity also affects solubility in common process solvents; the tetraoxo form may require hot polar aprotic solvents, while the enol notation does not automatically imply aqueous solubility. The material should not be dissolved in strongly alkaline aqueous media without stability data, because base-catalysed ring opening or salt formation may occur.
Application routes are typically confined to medicinal chemistry synthesis, coordination polymer assembly, and heterocyclic building-block storage. Synthetic use in medicinal chemistry often relies on the pyrimido[5,4-d]pyrimidine core as a purine mimetic or a hydrogen-bonding pharmacophore element. In coordination chemistry, the polyfunctional oxygen/nitrogen array can act as a multidentate ligand, but the accessible donor set depends on tautomer state and pH. The compound is not marketed as a formulated end product; any downstream use should be supported by a process-specific stability study under the intended solvent, temperature, and catalyst conditions.
