4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Base Information

• Chemical Name: 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine
• CAS No.: 479633-63-1
• Molecular Formula: C13H10ClN3O2S
• Molecular Weight: 307.76
• Hs Code.: 2933990090
• Mol file: 479633-63-1.mol

Synonyms:4-Chloro-7-(4-methylphenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine;

Chemical Property of 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

Chemical Property:

• Vapor Pressure: 2.46E-10mmHg at 25°C
• Melting Point: 145.0 to 149.0 °C
• Refractive Index: 1.696
• Boiling Point: 505.3 °C at 760 mmHg
• PKA: 1.73±0.30(Predicted)
• Flash Point: 259.4 °C
• PSA: 73.23000
• Density: 1.49 g/cm³
• LogP: 3.71090
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

98%, ^*data from raw suppliers

4-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidine >96.0%(HPLC)(N) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

There total 14 articles about 4-chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.7%

4-chloro-1H-pyrrolo[2,3-d]pyrimidine (3680-69-1) + p-toluenesulfonyl chloride (98-59-9) → 4-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (479633-63-1)

Guidance literature:

With sodium hydroxide; In water; acetone; at 0 - 20 ℃; for 6h;

Reference yield: 93.0%

2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (90213-66-4) + p-toluenesulfonyl chloride (98-59-9) → 4-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (479633-63-1)

Guidance literature:

With sodium hydroxide; In water; acetone; at 0 - 20 ℃; for 3h;

Reference yield: 92.0%

→ 4-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine (479633-63-1)

Guidance literature:

With sodium hydroxide; In water; acetone; at 0 - 20 ℃; for 1h;

upstream raw materials:

p-toluenesulfonyl chloride

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

6-chloro deazapurine

2-cyano-4,4-dimethoxybutyric acid ethyl ester

Downstream raw materials:

4-(2-chloro-imidazol-1-yl)-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

ethyl 7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine-4-carboxylate

7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine-4-carbonitrile

4-(4-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl)-7H-pyrrolo[2,3-d]pyrimidine

Refernces

• 1、 -. "PROCESS AND INTERMEDIATES FOR PREPARING A JAK INHIBITOR". . . Retrieved 2022/03/04.
• 2、 -. "Preparation method of key intermediate of JAK inhibitor". Paragraph 0043-0045; 0050-0052; 0057-0059. . Retrieved 2021/09/04.