Production Method 1

7355-55-7

84955-31-7

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: N,N-Dimethylaniline ;  reflux

Reference

Engineering Unnatural Nucleotide Specificity to Probe G Protein Signaling

Vincent, Fabien; Cook, Silas P.; Johnson, Emmanuel O.; Emmert, Dana; Shah, Kavita, Chemistry & Biology (Cambridge, 2007, 14(9), 1007-1018

Production Method 2

3680-69-1

84955-31-7

Reaction Conditions

1.1 Reagents: Ammonia ,  Potassium amide ;  -40 °C → -20 °C; 24 h
1.2 Reagents: Ammonium chloride

Reference

Synthesis, biological evaluation and molecular docking studies of novel pyrrolo[2,3-d]pyrimidin-2-amine derivatives as EGFR inhibitors

Sivaiah, G.; Raveesha, R.; Benaka Prasad, S. B.; Yogesh Kumar, K.; Raghu, M. S.; et al, Journal of Molecular Structure, 2023, 1275,

Production Method 3

7355-55-7

84955-31-7

Reaction Conditions

1.1 Solvents: Phosphorus oxychloride ;  2 h, reflux; reflux → rt
1.2 Solvents: Water ;  cooled
1.3 Reagents: Ammonia Solvents: Water ;  pH 2, cooled; 2 h, 0 °C

Reference

Synthesis of the transfer-RNA nucleoside queuosine by using a chiral allyl azide intermediate

Klepper, Florian; Jahn, Eva-Maria; Hickmann, Volker; Carell, Thomas, Angewandte Chemie, 2007, 46(13), 2325-2327

Production Method 4

7355-55-7

84955-31-7

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  2 h, rt → 115 °C; 115 °C → rt
1.2 Reagents: Water ;  rt
1.3 Reagents: Ammonia Solvents: Water ;  30 min, neutralized, 0 °C

Reference

Synthesis of Galactosyl-Queuosine and Distribution of Hyper-modified Q-Nucleosides in Mouse Tissues

Thumbs, Peter; Ensfelder, Timm T. ; Hillmeier, Markus; Wagner, Mirko ; Heiss, Matthias ; et al, Angewandte Chemie, 2020, 59(30), 12352-12356

4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine Raw materials

• 7-Deazaguanine
• 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine

4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine Preparation Products

• 4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7)

• 1. An aptasensor for the detection of ampicillin in milk using a personal glucose meter
  Xixi Li,Nanwei Zhu,Ruohan Li,Qinpu Zhang Anal. Methods, 2020,12, 3376-3381
• 2. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554
• 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 alumina stabilized graphene oxide wrapped SnO2 hollow sphere LIB anode with improved lithium storage?
  Xiang Liu,Qian Sun,A. B. Djuri?i?,Maohai Xie,Baohu Dai,Jinyao Tang,Charles Surya,Changzhong Liao,Kaimin Shih RSC Adv., 2015,5, 100783-100789
• 5. An automatic determination of thoria in thoria-urania mixtures
  Analyst, 1966,91, 208-210

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolopyrimidines Pyrrolo[2,3-d]pyrimidines

Comprehensive Overview of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (CAS No. 84955-31-7): Properties, Applications, and Research Insights

4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (CAS No. 84955-31-7) is a heterocyclic organic compound that has garnered significant attention in pharmaceutical and biochemical research due to its unique structural features and versatile applications. As a derivative of the pyrrolopyrimidine scaffold, this compound is widely studied for its potential role in drug discovery, particularly in the development of kinase inhibitors and anticancer agents. Researchers are increasingly exploring its structure-activity relationships (SAR) to optimize therapeutic efficacy.

The molecular formula of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine is C₆H₆ClN₅, with a molecular weight of 183.60 g/mol. Its pyrrolopyrimidine core is a privileged structure in medicinal chemistry, often associated with high binding affinity to biological targets. The presence of both chloro and amine functional groups allows for further derivatization, making it a valuable intermediate in synthetic chemistry. Recent studies highlight its relevance in targeted therapy, aligning with the growing demand for precision medicine.

In the context of current research trends, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine is frequently discussed in connection with JAK-STAT signaling pathway modulation. This pathway is critical in immune regulation and inflammation, making the compound a candidate for autoimmune disease research. Additionally, its potential applications in cancer immunotherapy have sparked interest, as scientists investigate its ability to synergize with checkpoint inhibitors. These topics resonate with frequent search queries like "pyrrolopyrimidine kinase inhibitors" and "small molecule immunomodulators."

From a synthetic perspective, the compound’s chloro-substitution at the 4-position enables nucleophilic aromatic substitution (S_NAr) reactions, facilitating the introduction of diverse pharmacophores. This reactivity is exploited in parallel synthesis workflows, a technique often searched by chemists under terms like "high-throughput medicinal chemistry." Furthermore, its amine group at the 2-position allows for coupling reactions, expanding its utility in fragment-based drug design (FBDD).

Environmental and regulatory considerations are also pivotal in discussions about 4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine. With increasing emphasis on green chemistry, researchers are optimizing synthetic routes to minimize hazardous byproducts. Searches related to "sustainable heterocyclic synthesis" reflect this trend. Moreover, the compound’s stability under physiological conditions is a key focus, addressing queries about "metabolic stability of pyrrolopyrimidines."

In summary, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (CAS No. 84955-31-7) represents a multifaceted tool in modern drug discovery. Its integration into cutting-edge therapeutic strategies and alignment with trending scientific inquiries underscore its enduring relevance. As the field advances, this compound is poised to remain at the forefront of small-molecule research, answering critical questions in both academia and industry.

• 1243346-92-0(6-Chloro-7-deazapurine Hydrochloride)
• 90994-17-5(6-Chloro-7H-pyrrolo2,3-dpyrimidine)
• 90065-71-7(4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine)
• 90358-16-0(4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-2-amine)
• 651035-58-4(1H-Pyrrolo[2,3-d]pyrimidin-2-amine, 4-chloro-, monosodium salt)
• 873792-86-0(7H-Pyrrolo[2,3-d]pyrimidin-2-amine,4,5-dichloro-)
• 3680-69-1(4-Chloro-7H-pyrrolo[2,3-d]pyrimidine)
• 28732-79-8(4-chloropyrido[2,3-d]pyrimidine)
• 204929-06-6(4-chloro-6-methyl-7H-Pyrrolo[2,3-d]pyrimidin-2-amine)
• 97337-32-1(4,6-Dichloro-7H-pyrrolo[2,3-d]pyrimidine)