876343-10-1

Basic information

• Product Name: 4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine
• Synonyms: 4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine;4-Chloro-6-iodo-7H-pyrrol...;4-chloro-6-iodo-7H-pyrrolo[2;4-chloro-6-iodo-1H-pyrrolo[2,3-d]pyrimidine
• CAS NO: 876343-10-1
• Molecular Formula: C₆H₃ClIN₃
• Molecular Weight: 279.47
• Product Categories: CHIRAL CHEMICALS;pyrimidine;Heterocycle-Pyrimidine series
• Mol File: 876343-10-1.mol

Chemical Properties

• Appearance: /
• Density: 2.284 g/cm³
• Refractive Index: 1.804
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 9.74±0.50(Predicted)
• CAS DataBase Reference: 4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine(876343-10-1)
• EPA Substance Registry System: 4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine(876343-10-1)

Safety Data

• Hazardous Substances Data: 876343-10-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine is used as a key building block for the synthesis of various pharmaceuticals. Its unique structure and reactivity allow for the creation of new compounds with potential therapeutic applications.
Used in Agrochemical Synthesis:
In the agrochemical industry, 4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine is utilized as a starting material for the development of new agrochemicals. Its structural properties contribute to the formulation of compounds that can be used in crop protection and other agricultural applications.
Used in Anti-Cancer Research:
4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine has been studied for its potential as an anti-cancer agent. Its biological activities are being investigated for possible use in the development of new cancer treatments.
Used in Metal-Catalyzed Reactions:
4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine also serves as a ligand in metal-catalyzed reactions, which are important in the synthesis of complex organic molecules. Its role in these reactions is crucial for the development of new chemical compounds with various applications.

InChI:InChI=1/C6H3ClIN3/c7-5-3-1-4(8)11-6(3)10-2-9-5/h1-2H,(H,9,10,11)

Upstream product

• 876343-09-8 7-(benzenesulfonyl)-4-chloro-6-iodo-7H-pyrrolo[2,3-d]pyrimidine 
• 3680-71-5 Allopurinol 
• 186519-89-1 7-(benzenesulfonyl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidine 
• 3680-71-5 7-deazahypoxanthine 

Downstream Products

• 1637437-41-2 C₁₄H₁₂FIN₄O 
• 1637438-20-0 C₂₁H₂₀N₄O 
• 1637438-32-4 C₂₀H₁₈N₄O 
• 1637438-64-2 C₂₀H₁₈N₄O 
• 1637569-24-4 C₂₁H₂₀N₄O 
• 497841-30-2 {3-[4-((R)-1-phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol 
• 497841-27-7 {4-[4-((R)-1-phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol 
• 1637437-71-8 (R)-3-methoxy-4-(4-((1-phenylethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzaldehyde 
• 1637437-39-8 (R)-(3-methoxy-4-(4-((1-phenylethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)phenyl)methanol 
• 1637438-12-0 (S)-2-((6-(2-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-2-phenylethan-1-ol 
• 1637437-61-6 (S)-2-((6-(4-(hydroxymethyl)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-2-phenylethan-1-ol 
• 1637438-04-0 (S)-4-(4-((2-hydroxy-1-phenylethyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3-methoxybenzaldehyde 
• 1637437-96-7 (S)-2-((6-(4-(hydroxymethyl)-2-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-2-phenylethan-1-ol 
• 1643962-37-1 (R)-6-iodo-N-(1-phenylethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 

Relevant articles and documents

IRREVERSIBLE INHIBITORS OF MENIN-MLL INTERACTION

Disclosed herein are heterocyclic compounds that inhibit the binding of menin and MLL or MLL fusion proteins. Also described are specific irreversible inhibitors of menin-MLL interaction. Also disclosed are pharmaceutical compositions that include the compounds. Methods of using the menin-MLL irreversible inhibitors are disclosed, alone or in combination with other therapeutic agents, for the treatment of autoimmune diseases or conditions, heteroimmune diseases or conditions, cancer, including lymphoma, leukemia and other diseases or conditions dependent on menin-MLL interaction.

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

The present study describes our continuous effort to develop epidermal growth factor receptor (EGFR) inhibitors based on the 6-aryl-pyrrolo[2,3-d]pyrimidin-4-amine scaffold. The activity-ADME space has been evaluated by synthesizing 43 new structures, including four variations of the 4-amino group and 34 different substitution patterns in the 6-aryl moiety. Most of the new pyrrolopyrimidines were highly active, with twelve analogues possessing lower IC50values than the commercial drug Erlotinib in enzymatic assays. Ten EGFR inhibitors were also profiled in cell studies using the Ba/F3-EGFRL858Rreporter cells, and all revealed nanomolar activity. However, some of the privileged structures in terms of potency had ADME short-comings: compounds containing amides, sulfonamides, amine and hydroxymethyl substituents in the 6-aryl group had low permeability and high efflux, derivatives having (R)-3-amino-3-phenylpropan-1-ol at C-4 induced hERG inhibition properties, and metabolic lability was seen for compounds having (S)-2-methoxy-1-phenylethan-1-amine at C-4. Based on a trade-off between enzymatic activity, cellular potency and ADME properties, (S)-2-phenyl-2-((6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethan-1-ol appeared as the most promising drug candidate. Cellular studies indicate this compound to have therapeutic use in EGFR driven diseases.

4-AMINO-6-ARYL[2,3-D]PYRIMIDINES FOR THE INHIBITION OF EGFR TYROSINE KINASE

This invention relates to certain new pyrrolo-, thieno-, and furo-[2,3- d]pyrimidine compounds, such as of general formula (I) These compounds are epidermal growth factor receptor tyrosine kinase inhibitors and therefore offer potential in the treatment of cancer.

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

The epidermal growth factor receptor is an important target in molecular cancer therapy. Herein, the enzymatic inhibition potential of a series of chiral and non chiral pyrrolopyrimidine based derivatives have been investigated and optimised. Overall, seven new compounds were identified having enzymatic IC 50 values comparable to or better than the commercial drug Erlotinib. High activity was also confirmed towards the epidermal growth factor receptor L858R and L861Q mutants. Based on calculated druglike properties, eight compounds were further evaluated towards a panel of 52 other kinases revealing interesting Src-family kinase and colony stimulating factor 1 receptor kinase inhibitory activity. Cell proliferation studies with the cell lines A431, C-33A, AU-565, K-562 and genetically engineered Ba/F3-EGFRL858R cells also showed several molecules to be more active than Erlotinib, and thus confirming these pyrrolopyrimidines as attractive drug candidates or lead structures.

ARYL-AMINO SUBSTITUTED PYRROLOPYRIMIDINE MULTI-KINASE INHIBITING COMPOUNDS

Compounds represented by Formula (I): or stereoisomers or pharmaceutically acceptable salts thereof, are inhibitors of least two of the Abl, Aurora-A, Blk, c-Raf, cSRC, Src, PRK2, FGFR3, Flt3, Lck, Mekl, PDK-1, GSK3?, EGFR, p70S6K, BMX, SGK, CaMKII, Tie-2