63200-54-4

Basic information

• Product Name: 2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE
• Synonyms: 2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE;2,4-Dichloropyrrolo[3,2-d]pyrimidine;2,4-Dichloro-5H-pyrrolo[3...;2-d]pyriMidine;4-dichloro-5H-pyrrolo[3;2,4-Dichl;5H-Pyrrolo[2,3-d]pyriMidine, 2,4-dichloro-;5H-Pyrrolo[3,2-d]pyriMidine,2,4-dichloro-
• CAS NO: 63200-54-4
• Molecular Formula: C₆H₃Cl₂N₃
• Molecular Weight: 188.01
• EINECS: 1312995-182-4
• Product Categories: Heterocycles;CHIRAL CHEMICALS;Heterocycle-Pyrimidine series
• Mol File: 63200-54-4.mol
• Article Data: 14

Chemical Properties

• Melting Point: 226-228 °C(Solv: water (7732-18-5); methanol (67-56-1))
• Boiling Point: 306.2±24.0 °C(Predicted)
• Appearance: /
• Density: 1.675 g/cm³
• Refractive Index: 1.724
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 10.67±0.40(Predicted)
• CAS DataBase Reference: 2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE(63200-54-4)
• EPA Substance Registry System: 2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE(63200-54-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 63200-54-4(Hazardous Substances Data)

Usage

General Description

2,4-Dichloro-5H-pyrollo[3,2-d]pyrimidine is a chemical compound that belongs to the class of organic compounds known as dichlorobenzenes. These are organochlorine compounds that contain exactly two chlorine atoms attached to a benzene moiety. Structurally, its chemical formula is C7H4Cl2N2, and it is characterized by a pyrrolopyrimidine core, a fused, bicyclic nitrogen-containing heterocycle. 2,4-DICHLORO-5H-PYRROLO[3,2-D]PYRIMIDINE is used in the synthesis of various pharmaceuticals and therapeutic agents due to its unique chemical properties, particularly in relation to its nitrogen-containing heterocyclic structure, making it a key intermediate in a variety of chemical reactions. Its two chlorine atoms also contribute to its reactivity. Further studies are conducted on this compound to fully explore its potential applications.

InChI:InChI=1/C6H3Cl2N3/c7-5-4-3(1-2-9-4)10-6(8)11-5/h1-2,9H

Upstream product

• 129872-83-9 5-benzyl-2,4-dichloro-5H-pyrrolo<3,2-d>pyrimidine 
• 65996-50-1 2,4-Dioxo-1,2,3,4-tetrahydropyrrolo<3,2-d>pyrimidine 

Downstream Products

• 114684-95-6 2-Chloro-4-piperidin-1-yl-5H-pyrrolo[3,2-d]pyrimidine 
• 114684-96-7 2-Chloro-4-morpholin-4-yl-5H-pyrrolo[3,2-d]pyrimidine 
• 561051-95-4 [4-(benzylamino)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]methanol 
• 914497-01-1 2-chloro-4-(4-cyclopropyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidine 

Relevant articles and documents

Structural and Biological Investigations for a Series of N-5 Substituted Pyrrolo[3,2-d]pyrimidines as Potential Anti-Cancer Therapeutics

Pyrrolo[3,2-d]pyrimidines have been studied for many years as potential lead compounds for the development of antiproliferative agents. Much of the focus has been on modifications to the pyrimidine ring, with enzymatic recognition often modulated by C2 and C4 substituents. In contrast, this work focuses on the N5 of the pyrrole ring by means of a series of novel N5-substituted pyrrolo[3,2-d]pyrimidines. The compounds were screened against the NCI-60 Human Tumor Cell Line panel, and the results were analyzed using the COMPARE algorithm to elucidate potential mechanisms of action. COMPARE analysis returned strong correlation to known DNA alkylators and groove binders, corroborating the hypothesis that these pyrrolo[3,2-d]pyrimidines act as DNA or RNA alkylators. In addition, N5 substitution reduced the EC50 against CCRF-CEM leukemia cells by up to 7-fold, indicating that this position is of interest in the development of antiproliferative lead compounds based on the pyrrolo[3,2-d]pyrimidine scaffold.

Pyrrolopyrimidine ketone compound and preparation method and application thereof

The invention relates to a pyrrolopyrimidine ketone compound and a preparation method and application thereof, and belongs to the technical field of medicine. The pyrrolopyrimidine ketone compound having a structural feature of formula I, or a pharmaceutically acceptable salt thereof has a very good inhibition effect on DPP-IV, and almost no effect on activity of DPP-VIII and DPP-IX, can effectively control the blood glucose concentration of diabetic rats, and is safe and low in toxicity through the verification of pharmacological and toxicological tests. After being prepared into a medicine, the compound provided by the invention not only has an obvious efficacy but also has very small side effects, thus greatly improving the administration convenience and patient use compliance, therefore, the compound has obvious advantages compared with the same kind of medicine. The formula is shown in the specification.

Antiproliferative activities of halogenated pyrrolo[3,2-d]pyrimidines

In vitro evaluation of the halogenated pyrrolo[3,2-d]pyrimidines identified antiproliferative activities in compounds 1 and 2 against four different cancer cell lines. Upon screening of a series of pyrrolo[3,2-d]pyrimidines, the 2,4-Cl compound 1 was foun