Production Method 1

186519-89-1

876343-09-8

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide ;  -78 °C; 1 h, -78 °C → -55 °C; -55 °C → -78 °C
1.2 Reagents: Iodine ;  1.5 h, -78 °C
1.3 Reagents: Ammonium chloride Solvents: Water ;  -20 °C

Reference

Novel hinge-binding motifs for janus kinase 3 inhibitors: a comprehensive structure-activity relationship study on tofacitinib bioisosteres

Gehringer, Matthias; et al, ChemMedChem, 2014, 9(11), 2516-2527

Production Method 2

3680-69-1

876343-09-8

Reaction Conditions

1.1 -
2.1 Reagents: Lithium diisopropylamide ;  -78 °C; 1 h, -78 °C → -55 °C; -55 °C → -78 °C
2.2 Reagents: Iodine ;  1.5 h, -78 °C
2.3 Reagents: Ammonium chloride Solvents: Water ;  -20 °C

Reference

Novel hinge-binding motifs for janus kinase 3 inhibitors: a comprehensive structure-activity relationship study on tofacitinib bioisosteres

Gehringer, Matthias; et al, ChemMedChem, 2014, 9(11), 2516-2527

Production Method 3

186519-89-1

876343-09-8

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  -78 °C; 1.5 h, -78 °C
1.2 Reagents: Iodine Solvents: Tetrahydrofuran ;  -78 °C; 3 h, -78 °C
1.3 Solvents: Water

Reference

Combating Drug-Resistant Mutants of Anaplastic Lymphoma Kinase with Potent and Selective Type-I1/2 Inhibitors by Stabilizing Unique DFG-Shifted Loop Conformation

Pan, Peichen; et al, ACS Central Science, 2017, 3(11), 1208-1220

Production Method 4

3680-71-5

876343-09-8

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  6 h, rt → 90 °C
1.2 Reagents: Water ;  cooled
1.3 Reagents: Sodium hydroxide ;  pH 12
2.1 Reagents: Sodium tert-butoxide Solvents: Tetrahydrofuran ;  rt → 10 °C
2.2 2 h, 22 °C
2.3 Reagents: Water ;  10 min, 22 °C
3.1 Reagents: Lithium diisopropylamide Solvents: Ethylbenzene ,  Tetrahydrofuran ,  Heptane ;  30 min, -78 °C; 1 h, -78 °C
3.2 Reagents: Iodine Solvents: Tetrahydrofuran ;  30 min, -78 °C; 1 h, -78 °C
3.3 Reagents: Hydrochloric acid Solvents: Water ;  22 °C

Reference

Identification of new 4-N-substituted 6-aryl-7H-pyrrolo[2,3-d]pyrimidine-4-amines as highly potent EGFR-TK inhibitors with Src-family activity

Kaspersen, Svein Jacob; et al, European Journal of Pharmaceutical Sciences, 2014, 59, 69-82

Production Method 5

186519-89-1

876343-09-8

Reaction Conditions

1.1 Reagents: Lithium diisopropylamide ,  Iodine Solvents: Tetrahydrofuran

Reference

Balancing potency, metabolic stability and permeability in pyrrolopyrimidine-based EGFR inhibitors

Han, Jin; et al, European Journal of Medicinal Chemistry, 2016, 124, 583-607

7-(benzenesulfonyl)-4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine Raw materials

• 7-(benzenesulfonyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
• 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
• 7-Deazahypoxanthine

7-(benzenesulfonyl)-4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine Preparation Products

• 7-(benzenesulfonyl)-4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine (876343-09-8)

• 1. Acetylcholinesterase amperometric detection system based on a cobalt(II) tetraphenylporphyrin-modified electrode
  Analyst, 1996,121, 1123-1126
• 2. An integrated digital microfluidic chip for multiplexed proteomic sample preparation and analysis by MALDI-MS?
  Hyejin Moon,Aaron R. Wheeler,Robin L. Garrell,Chang-Jin “CJ” Kim Lab Chip, 2006,6, 1213-1219
• 3. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
  Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?o Chem. Commun., 2015,51, 3993-3996
• 4. An amphoteric reactivity of a mixed-valent bis(μ-oxo)dimanganese(iii,iv) complex acting as an electrophile and a nucleophile?
  Muniyandi Sankaralingam,So Hyun Jeon,Yong-Min Lee,Mi Sook Seo,Wonwoo Nam Dalton Trans., 2016,45, 376-383
• 5. An atmosphere and light tuned highly diastereoselective synthesis of cyclobuta/penta[b]indoles from aniline-tethered alkylidenecyclopropanes with alkynes?
  Bo Cao,Yin Wei Chem. Commun., 2018,54, 2870-2873

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzenesulfonamides

Comprehensive Overview of 7-(benzenesulfonyl)-4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine (CAS No. 876343-09-8)

The compound 7-(benzenesulfonyl)-4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine (CAS No. 876343-09-8) is a highly specialized heterocyclic molecule that has garnered significant attention in the fields of medicinal chemistry and drug discovery. Its unique structural features, including the pyrrolo[2,3-d]pyrimidine core, benzenesulfonyl group, and halogen substitutions (chloro and iodo), make it a valuable scaffold for designing novel therapeutic agents. Researchers are particularly interested in its potential applications in targeting protein kinases and other enzymes involved in cellular signaling pathways.

In recent years, the demand for halogenated pyrrolopyrimidines has surged due to their role in developing kinase inhibitors, a class of drugs widely used in oncology and autoimmune diseases. The presence of the iodo substituent at the 6-position of the pyrrolo[2,3-d]pyrimidine ring enhances the compound's reactivity, enabling further functionalization through cross-coupling reactions such as Suzuki or Sonogashira couplings. This versatility aligns with the growing trend of fragment-based drug design (FBDD), where small molecular fragments are optimized to improve binding affinity and selectivity.

Another area of interest is the benzenesulfonyl moiety, which is known to improve the pharmacokinetic properties of drug candidates. Sulfonamide-containing compounds often exhibit enhanced metabolic stability and membrane permeability, making them attractive for oral drug delivery. The combination of the benzenesulfonyl group with the pyrrolo[2,3-d]pyrimidine core in CAS No. 876343-09-8 offers a balanced profile of lipophilicity and solubility, addressing one of the key challenges in modern drug development.

The synthetic accessibility of 7-(benzenesulfonyl)-4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine has also been a topic of discussion in academic and industrial circles. Efficient routes for its preparation often involve multi-step reactions, including halogenation and sulfonylation, with careful control of reaction conditions to ensure high yields and purity. This aligns with the broader industry focus on green chemistry and sustainable synthesis, where minimizing waste and optimizing atom economy are prioritized.

From a commercial perspective, the compound's CAS No. 876343-09-8 is frequently searched in databases by pharmaceutical researchers and suppliers specializing in building blocks for drug discovery. Its applications extend beyond kinase inhibitors, with potential uses in epigenetic modulators and antiviral agents, reflecting the diverse therapeutic areas where pyrrolopyrimidine derivatives are being explored. As the demand for targeted therapies grows, compounds like this are likely to remain in the spotlight for years to come.

In summary, 7-(benzenesulfonyl)-4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine represents a compelling example of how structural complexity can be harnessed for therapeutic innovation. Its relevance to kinase inhibitor development, fragment-based drug design, and green synthesis underscores its importance in contemporary medicinal chemistry. For researchers seeking to explore its full potential, further studies on its biological activity and derivatization pathways will be essential.

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