479633-63-1

Basic information

• Product Name: 4-CHLORO-7-TOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE
• Synonyms: 4-CHLORO-7-[(4-METHYLPHENYL)SULFONYL]-7H-PYRROLO[2,3-D]PYRIMIDINE;4-CHLORO-7-TOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE;4-Chloro-7-tosyl-7H-pyrro...;4-Chloro-7-[(4-methylbenzene)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine;4-Chloro-7-p-toluenesulphonyl-7H-pyrrolo[2,3-d]pyrimidine;7H-Pyrrolo[2,3-D]pyriMidine,4-chloro-7-[(4-Methylphenyl)sulfonyl]-;Tofacitinib Impurity R;4-Chloro-7-(p-tolylsulfonyl)pyrrolo[2,3-d]pyrimidine
• CAS NO: 479633-63-1
• Molecular Formula: C₁₃H₁₀ClN₃O₂S
• Molecular Weight: 307.76
• EINECS: 1312995-182-4
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 479633-63-1.mol
• Article Data: 29

Chemical Properties

• Melting Point: 145.0 to 149.0 °C
• Boiling Point: 505.3 °C at 760 mmHg
• Flash Point: 259.4 °C
• Appearance: /
• Density: 1.49
• Vapor Pressure: 2.46E-10mmHg at 25°C
• Refractive Index: 1.696
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 1.73±0.30(Predicted)
• CAS DataBase Reference: 4-CHLORO-7-TOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-7-TOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE(479633-63-1)
• EPA Substance Registry System: 4-CHLORO-7-TOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE(479633-63-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 479633-63-1(Hazardous Substances Data)

Usage

Uses

4-Chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine is a reagent in the synthesis of (+)-tofacitinib, a selective Janus kinase 3 inhibitor (JAK3) and an immunosuppressant drug.

InChI:InChI=1/C13H10ClN3O2S/c1-9-2-4-10(5-3-9)20(18,19)17-7-6-11-12(14)15-8-16-13(11)17/h2-8H,1H3

Upstream product

• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 98-59-9 p-toluenesulfonyl chloride 
• 7400-06-8 4-amino-6-hydroxy-5-(2,2-diethoxyethyl)pyrimidine 
• 3680-71-5 Allopurinol 
• 52133-67-2 ethyl 2-cyano-4,4-diethoxybutyrate 
• 1634-04-4 tert-butyl methyl ether 
• 1236033-25-2 (E)-6-chloro-5-(2-methoxyvinyl)pyrimidin-4-ylamine 
• 14160-93-1 4-amino-6-chloro-pyrimidine-5-carbaldehyde 
• 90213-66-4 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine 
• 773076-83-8 2-cyano-4,4-dimethoxybutyric acid ethyl ester 
• 3680-69-1 6-chloro deazapurine 

Downstream Products

• 910789-32-1 methyl-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine 
• 911122-34-4 4-(2-chloro-imidazol-1-yl)-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

Identification of N-Phenyl-7 H-pyrrolo[2,3- d]pyrimidin-4-amine Derivatives as Novel, Potent, and Selective NF-κB Inducing Kinase (NIK) Inhibitors for the Treatment of Psoriasis

A series of N-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine derivatives with NF-κB inducing kinase (NIK) inhibitory activity were obtained through structure-based drug design and synthetic chemistry. Among them, 4-(3-((7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-4-morpholinophenyl)-2-(thiazol-2-yl)but-3-yn-2-ol (12f) was identified as a highly potent NIK inhibitor, along with satisfactory selectivity. The pharmacokinetics of 12f and its ability to inhibit interleukin 6 secretion in BEAS-2B cells were better than compound 1 developed by Amgen. Oral administration of different doses of 12f in an imiquimod-induced psoriasis mouse model showed effective alleviation of psoriasis, including invasive erythema, swelling, skin thickening, and scales. The underlying pathological mechanism involved attenuation of proinflammatory cytokine and chemokine gene expression, and the infiltration of macrophages after the treatment of 12f. This work provides a foundation for the development of NIK inhibitors, highlighting the potential of developing NIK inhibitors as a new strategy for the treatment of psoriasis.

PROCESS AND INTERMEDIATES FOR PREPARING A JAK INHIBITOR

The present invention is related to processes for preparing ruxolitinib, or a salt thereof, and related synthetic intermediates related thereto.

Selective JAK1 inhibitor compound as well as preparation method and application thereof

The invention provides a heterocyclic compound serving as a JAK1 inhibitor and synthesis and use methods, and particularly provides a compound shown as a formula (I), a preparation method of the compound and application of the compound serving as a JAK1 i