4-(Methylsulfanyl)-7-pentofuranosyl-7h-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Base Information

• Chemical Name: 4-(Methylsulfanyl)-7-pentofuranosyl-7h-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• CAS No.: 51112-63-1
• Molecular Formula: C13H14N4O4S
• Molecular Weight: 322.3397
• NSC Number: 116098
• DSSTox Substance ID: DTXSID30297466
• Mol file: 51112-63-1.mol

Synonyms:51112-63-1;NSC116098;4-(methylsulfanyl)-7-pentofuranosyl-7h-pyrrolo[2,3-d]pyrimidine-5-carbonitrile;DTXSID30297466;NSC-116098;7H-Pyrrolo[2, 4-(methylthio)- 7-beta-D-ribofuranosyl-

Chemical Property of 4-(Methylsulfanyl)-7-pentofuranosyl-7h-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Chemical Property:

• Vapor Pressure: 1.33E-19mmHg at 25°C
• Boiling Point: 683.2°C at 760 mmHg
• Flash Point: 367°C
• Density: 1.73g/cm³
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 322.07357611
• Heavy Atom Count: 22
• Complexity: 461

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CSC1=NC=NC2=C1C(=CN2C3C(C(C(O3)CO)O)O)C#N

Technology Process of 4-(Methylsulfanyl)-7-pentofuranosyl-7h-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

There total 6 articles about 4-(Methylsulfanyl)-7-pentofuranosyl-7h-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 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: 72.0%

4-chloro-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile (52443-16-0) + sodium thiomethoxide (5188-07-8) → 4-methylthio-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile (51112-63-1)

Guidance literature:

In isopropyl alcohol; for 1h; Heating;

DOI:10.1016/j.bioorg.2006.07.003

Reference yield:

3,4-dihydro-4-oxo-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile (57071-68-8) → 4-methylthio-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile (51112-63-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / phosphorous oxychloride / 1 h / Heating

2: 81.5 percent / ammonia; methanol / 2.5 h / 5 °C

3: 72 percent / propan-2-ol / 1 h / Heating

With methanol; ammonia; trichlorophosphate; In isopropyl alcohol;

DOI:10.1016/j.bioorg.2006.07.003

Reference yield:

4-chloro-5-cyano-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine (57071-52-0) → 4-methylthio-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile (51112-63-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81.5 percent / ammonia; methanol / 2.5 h / 5 °C

2: 72 percent / propan-2-ol / 1 h / Heating

With methanol; ammonia; In isopropyl alcohol;

DOI:10.1016/j.bioorg.2006.07.003

upstream raw materials:

4-chloro-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile

sodium thiomethoxide

3,4-dihydro-4-oxo-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile

4-chloro-5-cyano-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine

Refernces