![4-(1H-Pyrazol-4-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine](/upload/1124/V61853.png)
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| Targets |
This compound is not a drug itself but rather a synthetic intermediate used in the preparation of JAK inhibitors, particularly ruxolitinib (INCB018424). Its "target" in a research context is the JAK-STAT signaling pathway, as the final drug products inhibit JAK1 and JAK2 kinases. Ruxolitinib, derived from this intermediate, is a potent JAK1/JAK2 inhibitor used in the treatment of myelofibrosis and polycythemia vera. The pyrrolo[2,3-d]pyrimidine scaffold is a privileged structure for kinase inhibitor design.
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| ln Vitro |
In vitro, the compound itself does not possess intrinsic biological activity as a drug; rather, it is a chemical precursor. However, the downstream products synthesized from this intermediate (e.g., ruxolitinib) show potent JAK1/JAK2 inhibitory activity. Ruxolitinib inhibits JAK1 and JAK2 with IC₅₀ values in the nanomolar range, blocking STAT phosphorylation and downstream signaling. The pyrrolo[2,3-d]pyrimidine core and pyrazole moiety are essential for kinase binding and activity. The compound is used as a reference standard or impurity marker in pharmaceutical quality control.
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| ln Vivo |
In vivo, this compound is not administered as a therapeutic agent. However, its downstream product ruxolitinib has demonstrated significant efficacy in preclinical models of myeloproliferative neoplasms and in clinical trials for myelofibrosis and polycythemia vera. Ruxolitinib reduces splenomegaly, improves constitutional symptoms, and prolongs survival in patients with myelofibrosis. The JAK-STAT pathway inhibition mediated by ruxolitinib has also been studied in inflammatory conditions and graft-versus-host disease.
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| Enzyme Assay |
Non-cell-based assays for this compound primarily involve its use as a reference standard or starting material in chemical synthesis. Analytical methods including HPLC, LC-MS, and NMR are used to characterize the compound's purity, identity, and stability. The compound serves as a quality control standard in the manufacturing of ruxolitinib. Its chemical properties (molecular weight 315.45, formula C₁₅H₂₁N₅OSi) are determined using standard physicochemical characterization techniques. The compound is also used in synthetic chemistry optimization studies.
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| Cell Assay |
As a biochemical reagent and synthetic intermediate, this compound is not used directly in cellular assays. However, the compound can be deprotected to yield the corresponding pyrrolo[2,3-d]pyrimidine intermediate for further functionalization and biological testing. The compound's role in cellular assays is as a precursor for the synthesis of JAK inhibitors, which are then tested in cell-based assays measuring JAK-STAT signaling inhibition. Phospho-STAT ELISA or Western blot assays are used to evaluate JAK inhibitor activity in cell lines treated with the final drug products.
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| Animal Protocol |
This compound is not used in animal experiments directly. It is a chemical intermediate for the synthesis of pharmaceutical compounds that are subsequently evaluated in animal models. Ruxolitinib (derived from this intermediate) is tested in xenograft models of myeloproliferative neoplasms, where it demonstrates tumor growth inhibition, reduction in inflammatory cytokines, and improvement in survival. Animal studies with ruxolitinib have been conducted in mice and rats to assess efficacy, pharmacokinetics, and toxicity. The compound itself is used only in chemical synthesis and quality control.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties are not applicable to this synthetic intermediate as it is not a therapeutic agent. However, the downstream drug ruxolitinib has well-characterized PK properties. Ruxolitinib is orally bioavailable, with a half-life of approximately 3 hours. It is metabolized primarily by CYP3A4 and has moderate protein binding. The compound's (4-(1H-Pyrazol-4-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine) chemical stability and solubility are characterized for its use as a synthetic building block.
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| Toxicity/Toxicokinetics |
The toxicity of this compound has not been characterized as it is not a therapeutic agent. However, the compound is handled as a chemical reagent with standard laboratory safety precautions. As an organic compound containing nitrogen and silicon, appropriate handling procedures should be followed to avoid inhalation, skin contact, or ingestion. The compound is classified as a biochemical reagent for research use only. Safety data sheets recommend standard protective measures including gloves, lab coat, and eye protection when handling the compound.
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| Additional Infomation |
4-(1H-Pyrazol-4-yl)-7-[[2-(trimethylsilyl)ethoxy]methyl]-7H-pyrrolo[2,3-d]pyrimidine (CAS# 941685-27-4) is a synthetic intermediate used in the preparation of the JAK inhibitor ruxolitinib (INCB018424). It has the molecular formula C₁₅H₂₁N₅OSi and a molecular weight of 315.45. The compound contains a trimethylsilyl-protected ethoxymethyl (SEM) group at the 7-position of the pyrrolo[2,3-d]pyrimidine core, which serves as a protecting group during synthesis. It is available as a biochemical reagent for research purposes and is not intended for human therapeutic use. The compound is also known as Ruxolitinib impurity and is used as a reference standard in pharmaceutical quality control.
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| Molecular Formula |
C15H21N5OSI
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| Molecular Weight |
315.45
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| Exact Mass |
315.151
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| CAS # |
941685-27-4
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| PubChem CID |
42631346
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| Appearance |
White to off-white solid powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
501.8±50.0 °C at 760 mmHg
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| Flash Point |
257.3±30.1 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.607
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| LogP |
2.45
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
22
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| Complexity |
364
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| Defined Atom Stereocenter Count |
0
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| SMILES |
N1NC=C(C2C3C=CN(C=3N=CN=2)COCC[Si](C)(C)C)C=1
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| InChi Key |
AVMLPTWVYQXRSV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H21N5OSi/c1-22(2,3)7-6-21-11-20-5-4-13-14(12-8-18-19-9-12)16-10-17-15(13)20/h4-5,8-10H,6-7,11H2,1-3H3,(H,18,19)
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| Chemical Name |
trimethyl-[2-[[4-(1H-pyrazol-4-yl)pyrrolo[2,3-d]pyrimidin-7-yl]methoxy]ethyl]silane
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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 |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 3.1701 mL | 15.8504 mL | 31.7007 mL | |
| 5 mM | 0.6340 mL | 3.1701 mL | 6.3401 mL | |
| 10 mM | 0.3170 mL | 1.5850 mL | 3.1701 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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