900789-14-2

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine is utilized as a key intermediate in the synthesis of pharmaceuticals for its ability to inhibit certain enzymes. This makes it instrumental in the development of new drugs that target specific biological pathways, potentially leading to treatments for various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine is employed as a building block in the creation of agrochemicals. Its incorporation into these products can contribute to the development of more effective pesticides, herbicides, and other agricultural chemicals that enhance crop protection and yield.
Used in Organic Chemistry Research:
5-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine is also used as a research compound in organic chemistry. Its unique structure and reactivity make it a subject of interest for scientists exploring new reactions, mechanisms, and the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
Within the field of medicinal chemistry, 5-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine is applied as a precursor in the synthesis of biologically active molecules. Its potential to be modified and incorporated into diverse chemical entities makes it a valuable tool for the design and discovery of new pharmaceutical agents with improved therapeutic properties.

InChI:InChI=1/C6H2BrCl2N3/c7-2-1-10-5-3(2)4(8)11-6(9)12-5/h1H,(H,10,11,12)

Upstream product

• 90213-66-4 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine 

Downstream Products

• 1053228-32-2 5-bromo-2,4-dichloro-7-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 1060815-86-2 2,4-dichloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine 

Relevant academic research and scientific papers

Synthetic method of 5-bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine

The invention provides a synthetic method of 5-bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine. 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine is dissolved in tetrahydrofuran, N-bromsucciniamide is added at theroom temperature, and stirring is conducted for 1-2 h; filtering, washing and ethanol recrystallization are conducted to obtain the pure 5-bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine is obtained; the pure 5-bromo-2,4-dichloro -7H-pyrrolo[2,3-d]pyrimidine, zinc powder and acetic acid are mixed, a heating reflux reaction is conducted, filtering is conducted, ethyl alcohol is removed by steaming,dissolving is conducted through an organic solvent, washing is conducted through a saturated sodium bicarbonate aqueous solution, washing is conducted through saturated salt, drying is conducted, drying by distillation is conducted, and a coarse product is obtained; and a pure product is obtained from the coarse product through ethane recrystallization. According to the synthetic method of the 5-bromo-2-chloro-7H-pyrrolo[2,3-d]pyrimidine, commercially-available raw materials are subjected to bromination and reduction reaction to generate the pure product; the raw materials are supplied commercially in large amount, are cheap and easy to obtain, auxiliary materials can be recycled and reused, the cost is obviously lowered, meanwhile pollution of toxic substances to the environment in the production process is avoided, and the safety in the operation process is improved; and the yield is greatly increased, the time is effectively shortened, operation is easy, and the post-processing process is simplified.

2,4-DISUBSTITUTED 7H-PYRROLO[2,3-D]PYRIMIDINE DERIVATIVE, PREPARATION METHOD AND MEDICINAL USE THEREOF

The present invention relates to a 2,4-disubstituted 7H-pyrrolo[2,3-d]pyrimidine derivative, a preparation method and a medicinal use thereof. In particular, the present invention discloses a compound of formula (I) or a pharmaceutically acceptable salt, stereoisomer, solvate or prodrug thereof, and a preparation method and use thereof. For the definition of each group in formula (I), see the description for details.

INHIBITORS OF PROTEIN KINASES

The present invention is directed to compounds of formula (I)-(II) and pharmaceutically acceptable salts, esters, and prodrugs thereof which are inhibitors of syk and/or JAK kinase. The present invention is also directed to intermediates used in making such compounds, the preparation of such a compound, pharmaceutical compositions containing such a compound, methods of inhibition syk and/or JAK kinase activity, methods of inhibition the platelet aggregation, and methods to prevent or treat a number of conditions mediated at least in part by syk and/or JAK kinase activity, such as undesired thrombosis and Non Hodgkin's Lymphoma.

7-Halogenated 7-deazapurine 2′-deoxyribonucleosides related to 2′-deoxyadenosine, 2′-deoxyxanthosine, and 2′- deoxyisoguanosine: Syntheses and properties

A series of 7-fluorinated 7-deazapurine 2′-deoxyribonucleosides related to 2′-deoxyadenosine, 2′-deoxyxanthosine, and 2′-deoxyisoguanosine as well as intermediates 4b - 7b, 8, 9b, 10b, and 17b were synthesized. The 7-fluoro substituent was introduced in 2,6-dichloro-7-deaza-9H-purine (11a) with Selectfluor (Scheme 1). Apart from 2,6-dichloro-7-fluoro-7-deaza-9H-purine (11b), the 7-chloro compound 11c was formed as by-product. The mixture 11b/11c was used for the glycosylation reaction; the separation of the 7-fluoro from the 7-chloro compound was performed on the level of the unprotected nucleosides. Other halogen substituents were introduced with N-halogenosuccinimides (11a→11c - 11e). Nucleobase-anion glycosylation afforded the nucleoside intermediates 13a - 13e (Scheme 2). The 7-fluoro- and the 7-chloro-7-deaza-2′-deoxyxanthosines, 5b and 5c, respectively, were obtained from the corresponding MeO compounds 17b and 17c, or 18 (Scheme 6). The 2′-deoxyisoguanosine derivative 4b was prepared from 2-chloro-7-fluoro-7-deaza-2′-deoxyadenosine 6b via a photochemically induced nucleophilic displacement reaction (Scheme 5). The pKa values of the halogenated nucleosides were determined (Table 3). 13C-NMR Chemical-shift dependencies of C(7), C(5), and C(8) were related to the electronegativity of the 7-halogen substituents (Fig. 3). In aqueous solution, 7-halogenated 2′-deoxyribonucleosides show an approximately 70% S population (Fig. 2 and Table 1).