![2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine](/upload/1124/V68653.png)
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| Targets |
2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine does not have a defined biological target as a building block. However, the 7-deazapurine scaffold (after substitution) can target a variety of enzymes and receptors that recognize purines. These include: adenosine receptors (A1, A2A, A2B, A3), protein kinases (e.g., JAK, BTK, PI3K, EGFR), phosphodiesterases, and nucleoside transporters. The chlorine substituents are placeholders for installing pharmacophoric groups that enhance binding affinity and selectivity. Known drugs containing this scaffold include the JAK inhibitor ruxolitinib and various anticancer agents.
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| ln Vitro |
90213-66-4|Reference Standard for Tofacitinib Impurity 08
The compound itself has no direct in vitro biological activity; the chlorines are required for subsequent substitution but are not optimized for receptor binding. After substitution (e.g., with an aniline or an amine), the resulting compounds may show potent kinase inhibition (IC50 in the nM range). For example, ruxolitinib (a JAK1/2 inhibitor) has IC50 values of 2.7 nM (JAK1) and 4.5 nM (JAK2). No activity for the dichloro building block. |
| ln Vivo |
No in vivo activity data are available for the building block. Kinase inhibitors derived from this scaffold have been evaluated in animal models of cancer (e.g., mouse xenografts of myelofibrosis or leukemia), inflammation (e.g., collagen-induced arthritis), and autoimmune diseases. Ruxolitinib is FDA-approved for myelofibrosis and polycythemia vera. No data for the building block.
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| Enzyme Assay |
The compound is not used directly in binding assays. For nucleophilic substitution, a typical protocol: To a solution of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (1 eq, 5 mmol) in anhydrous DMF (20 mL) at 0degC, add NaH (60% in oil, 1.1 eq) to deprotonate the N7-H. After 30 minutes, add an alkylating agent (e.g., benzyl bromide, 1.1 eq). Stir at room temperature for 12 hours. Quench with water, extract with EtOAc, and purify by column chromatography to obtain 7-alkylated product. Subsequent regioselective amination at C-4 or C-2 can be performed. No biological assays.
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| Cell Assay |
No cell-based protocols are established for the building block. For kinase inhibitors derived from it, typical cell-based assays include: cancer cell viability (e.g., HEL cells for JAK2-driven myelofibrosis) treated with test compound (0.1 nM - 10 uM) for 72 hours, measuring viability by CellTiter-Glo. Phosphorylation of STAT3 or STAT5 is measured by Western blot or flow cytometry after 2-6 hours of treatment. IC50 values for cellular activity often correlate with enzyme inhibition. The building block is not used.
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| Animal Protocol |
No animal studies have been conducted with the building block. For ruxolitinib and analogs, typical in vivo studies: BALB/c mice are injected with Ba/F3-JAK2V617F cells (5×10⁶) subcutaneously. When tumors reach 100-150 mm3, mice are treated orally with test compound (15-30 mg/kg twice daily) for 14 days. Tumor volume and body weight are measured. Spleen weight and hematocrit are also measured as pharmacodynamic markers. The building block is not administered.
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| ADME/Pharmacokinetics |
No PK data are available for 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine. It is not a drug candidate. If administered (which it is not), the compound would likely undergo rapid nucleophilic substitution with glutathione or other thiols, leading to detoxification. No ADME studies reported. Soluble in DMSO, DMF, and THF. Storage: powder at -20degC, protect from light and moisture.
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| Toxicity/Toxicokinetics |
Safety: May cause skin and eye irritation. Harmful if swallowed (estimated LD50 >2000 mg/kg). Not classified as carcinogen or mutagen. Use standard PPE: gloves, lab coat, safety goggles, fume hood. Avoid inhalation of dust. Stable under recommended storage conditions.
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| Additional Infomation |
2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine is not an approved drug and has no clinical trial history. It is a research chemical for pharmaceutical synthesis. It is a critical intermediate for the synthesis of JAK inhibitors (ruxolitinib, baricitinib, tofacitinib analogs), EGFR inhibitors (osimertinib), and other protein kinase inhibitors. The 7-deazapurine ring system is also used in the design of antiviral nucleoside analogs (e.g., against HCV, HIV, and Ebola virus). This building block is commercially available from chemical suppliers and is used extensively in medicinal chemistry campaigns to generate compound libraries for high-throughput screening. No approved drug contains the unprotected 2,4-dichloro form; the chlorine atoms are always substituted in the final drug molecule. The compound is for research use only.
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| Molecular Formula |
C6H3CL2N3
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| Molecular Weight |
188.01
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| Exact Mass |
186.97
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| CAS # |
90213-66-4
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| PubChem CID |
14116871
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| Appearance |
Off-white to yellow solid powder
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| Density |
1.7±0.1 g/cm3
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| Boiling Point |
306.2±24.0 °C at 760 mmHg
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| Melting Point |
247-250ºC
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| Flash Point |
167.7±8.5 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.724
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| LogP |
2.3
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
155
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClC1N=C2C(C=CN2)=C(Cl)N=1
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| InChi Key |
GHXBPCSSQOKKGB-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H3Cl2N3/c7-4-3-1-2-9-5(3)11-6(8)10-4/h1-2H,(H,9,10,11)
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| Chemical Name |
2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
H2O: < 0.1 mg/mL
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.3189 mL | 26.5943 mL | 53.1887 mL | |
| 5 mM | 1.0638 mL | 5.3189 mL | 10.6377 mL | |
| 10 mM | 0.5319 mL | 2.6594 mL | 5.3189 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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