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4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine is a heterocyclic chemical compound characterized by a molecular formula of C6H3Cl2N3. It features a unique fused ring system comprising a pyrrole and a pyrimidine, which endows it with versatile chemical properties and potential applications in various fields.

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  • 115093-90-8 Structure
  • Basic information

    1. Product Name: 4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine
    2. Synonyms: 4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine;5-Chloro-4-chloro-7H-pyrrolo[2,3-d]pyrimidine;5-Chloro-4-chloro-7H-pyrr...
    3. CAS NO:115093-90-8
    4. Molecular Formula: C6H3Cl2N3
    5. Molecular Weight: 188.01
    6. EINECS: N/A
    7. Product Categories: CHIRAL CHEMICALS;Heterocycle-Pyrimidine series
    8. Mol File: 115093-90-8.mol
  • Chemical Properties

    1. Melting Point: 290 °C
    2. Boiling Point: 361.101 °C at 760 mmHg
    3. Flash Point: 203.556 °C
    4. Appearance: /
    5. Density: 1.675 g/cm3
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 1.724
    8. Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
    9. Solubility: N/A
    10. PKA: 9.52±0.20(Predicted)
    11. CAS DataBase Reference: 4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine(CAS DataBase Reference)
    12. NIST Chemistry Reference: 4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine(115093-90-8)
    13. EPA Substance Registry System: 4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine(115093-90-8)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 115093-90-8(Hazardous Substances Data)

115093-90-8 Usage

Uses

Used in Pharmaceutical Industry:
4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine serves as a crucial building block in the synthesis of pharmaceutical drugs. Its unique structure allows for the development of new drugs with potential therapeutic applications, particularly in the area of anti-cancer research.
4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine is used as a precursor in drug development for its potential anti-cancer properties. It has been studied for its ability to target and inhibit specific biological pathways involved in cancer progression, making it a promising candidate for the creation of novel cancer therapeutics.
Used in Agrochemical Industry:
In the agrochemical sector, 4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine is utilized as a key component in the synthesis of various agrochemicals. Its incorporation into these products can enhance their effectiveness in protecting crops from pests and diseases, thereby contributing to increased agricultural productivity.
Used in Organic Synthesis:
4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine also functions as a reagent in organic synthesis. Its distinctive chemical properties make it a valuable tool for chemists in the preparation of a wide range of organic compounds, expanding the scope of chemical research and development.
Used as a Precursor in Chemical Manufacturing:
Furthermore, 4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine is employed as a precursor in the manufacturing of other chemical compounds. Its versatility and reactivity in chemical reactions facilitate the production of various specialty chemicals used across different industries, such as dyes, pigments, and advanced materials.

Check Digit Verification of cas no

The CAS Registry Mumber 115093-90-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,5,0,9 and 3 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 115093-90:
(8*1)+(7*1)+(6*5)+(5*0)+(4*9)+(3*3)+(2*9)+(1*0)=108
108 % 10 = 8
So 115093-90-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H3Cl2N3/c7-3-1-9-6-4(3)5(8)10-2-11-6/h1-2H,(H,9,10,11)

115093-90-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4,5-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

1.2 Other means of identification

Product number -
Other names 4,5-dichloropyrrolopyrimidine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:115093-90-8 SDS

115093-90-8Relevant articles and documents

Synthesis and anti-HBV activity of carbocyclic nucleoside hybrids with salient features of entecavir and aristeromycin

Baba, Masanori,Bal, Chandralata,Jha, Ashok Kumar,Neeladri, Seshubabu,Pallaka, Renuka Sivasankar,Samunuri, Ramakrishnamraju,Toyama, Masaaki

, p. 597 - 601 (2020)

Modified carbocyclic nucleosides (4a-g) constituting 7-deazapurine, 4′-methyl, exocyclic double bond and 2′,3′-hydroxy were synthesized. NOE and X-ray studies of4cconfirmed the α-configuration of 4′-methyl. The anti-HBV assay demonstrated4e(IC50/sub

Efficient and practical synthesis of 5′-deoxytubercidin and its analogues via Vorbrggen glycosylation

Song, Yang,Ding, Haixin,Dou, Yanhui,Yang, Ruchun,Sun, Qi,Xiao, Qiang,Ju, Yong

, p. 1442 - 1446 (2011)

An efficient and practical synthesis of naturally occurring marine nucleosides 5′-deoxytubercidins on a 10 gram scale in good overall yield is reported. The key step was the Vorbrggen glycosylation of pyrrolo[2,3-d]pyrimidines with 5-deoxy-1,2,3-tri-O-ace

Efficient halogenation synthesis method of aryl halide

-

Paragraph 0120-0123, (2021/03/31)

The invention discloses an efficient halogenation synthesis method of aryl halide. The method comprises the following step: in the presence of a catalyst (sulfoxide or oxynitride), a halogenation reagent and a solvent, carrying out a halogenation reaction on an aromatic ring compound to obtain the aryl halide. According to the present invention, in the presence of a catalyst (sulfoxide or nitrogenoxide), a halogenation reagent and a solvent, the aromatic ring is subjected to an efficient halogenation reaction, such that the very useful aryl halide can be obtained with high activity and high selectivity; and by adopting the method disclosed by the invention, aryl halides can be efficiently synthesized, and the method has a wide application prospect in actual production.

Scaffold-hopping identifies furano[2,3-d]pyrimidine amides as potent Notum inhibitors

Atkinson, Benjamin N.,Bayle, Elliott D.,Bictash, Magda,Fish, Paul V.,Frew, Sarah,Jeganathan, Fiona,Jones, E. Yvonne,Mahy, William,Monaghan, Amy,Papageorgiou, George,Sipthorp, James,Steadman, David,Svensson, Fredrik,Zhao, Yuguang

supporting information, (2020/01/03)

The carboxylesterase Notum is a key negative regulator of the Wnt signaling pathway by mediating the depalmitoleoylation of Wnt proteins. Our objective was to discover potent small molecule inhibitors of Notum suitable for exploring the regulation of Wnt signaling in the central nervous system. Scaffold-hopping from thienopyrimidine acids 1 and 2, supported by X-ray structure determination, identified 3-methylimidazolin-4-one amides 20–24 as potent inhibitors of Notum with activity across three orthogonal assay formats (biochemical, extra-cellular, occupancy). A preferred example 24 demonstrated good stability in mouse microsomes and plasma, and cell permeability in the MDCK-MDR1 assay albeit with modest P-gp mediated efflux. Pharmacokinetic studies with 24 were performed in vivo in mouse with single oral administration of 24 showing good plasma exposure and reasonable CNS penetration. We propose that 24 is a new chemical tool suitable for cellular studies to explore the fundamental biology of Notum.

ASK1 INHIBITING PYRROLOPYRIMIDINE AND PYRROLOPYRIDINE DERIVATIVES

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Paragraph 0165, (2019/02/02)

The present invention relates to pyrrolopyrimidine compounds according to Formula (I) and their use in the prophylaxis and/or treatment of pain, inflammatory conditions, cardiovascular diseases, neurodegenerative diseases, neurological diseases, complications of type I diabetes, cancer and/or fibrotic diseases. In a particular aspect, the present compounds are ASK inhibitors, particularly ASK1 inhibitors. The present invention also provides methods for the production of a compound of the invention, pharmaceutical compositions comprising a compound of the invention, the use of the compounds in the prophylaxis and/or treatment of pain, inflammatory conditions, cardiovascular diseases, neurodegenerative diseases, neurological diseases, complications of type I diabetes, cancer and/or fibrotic diseases. (Formula (I))

Piperidine-containing pyrrolopyrimidine compound and preparation method and application thereof

-

Paragraph 0101-0105, (2018/04/01)

The invention discloses a piperidine-containing pyrrolopyrimidine compound and a preparation method and application thereof. The piperidine-containing pyrrolopyrimidine compound adopts the structure shown in the general formula (I) or (II). The invention

Structural optimization elaborates novel potent Akt inhibitors with promising anticancer activity

Liu, Yang,Yin, Yanzhen,Zhang, Zhen,Li, Carrie J.,Zhang, Hui,Zhang, Daoguang,Jiang, Changying,Nomie, Krystle,Zhang, Liang,Wang, Michael L.,Zhao, Guisen

, p. 543 - 551 (2017/07/12)

Targeting of Akt has been validated as a well rationalized approach to cancer treatment, and represents a promising therapeutic strategy for aggressive hematologic malignancies. We describe herein an exploration of novel Akt inhibitors for cancer therapy through structural optimization of previously described 4-(piperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine derivatives. Our studies yielded a novel series of pyrrolopyrimidine based phenylpiperidine carboxamides capable of potent inhibition of Akt1. Notably, 10h exhibited robust antiproliferative effects in both mantle cell lymphoma cell lines and primary patient tumor cells. Low micromolar doses of 10h induced cell apoptosis and cell cycle arrest in G2/M phase, and significantly downregulated the phosphorylation of Akt downstream effectors GSK3β and S6 in Jeko-1 cells.

Discovery of 4-(Piperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine Derivatives as Akt Inhibitors

Liu, Yang,Yin, Yanzhen,Zhang, Jingya,Nomie, Krystle,Zhang, Liang,Yang, Dezhi,Wang, Michael L.,Zhao, Guisen

, p. 356 - 362 (2016/05/19)

A series of 4-(piperazin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine derivatives was synthesized and evaluated as Akt inhibitors by optimization of a weak screening lead (1). Typically, compounds 5q and 5t significantly improved the Akt1 inhibitory potency with IC

4'-SUBSTITUTED NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS

-

Page/Page column 50; 51, (2015/12/08)

Provided is 4'-substituted nucleoside derivatives of Formula I and their use in the inhibition of HIV reverse transcriptase, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS and/or ARC.

Discovery of a 4-aryloxy-1H-pyrrolo[3,2-c]pyridine and a 1-aryloxyisoquinoline series of TRPA1 antagonists

Hu, Yun-Jin,St.-Onge, Miguel,Laliberté, Sébastien,Vallée, Frédéric,Jin, Shujuan,Bedard, Leanne,Labrecque, Jean,Albert, Jeffrey S.

supporting information, p. 3199 - 3203 (2015/02/19)

A series of TRPA1 antagonists is described having a 4-aryloxy-1H-pyrrolo[3,2-c]pyridine or a 1-aryloxyisoquinoline scaffold. These compounds have high ligand efficiency and favorable physical properties and may thus serve as scaffolds for further optimization.

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