4-(2,6-Dioxo-1-propyl-3,7-dihydropurin-8-yl)benzenesulfonic acid

Base Information

• Chemical Name: 4-(2,6-Dioxo-1-propyl-3,7-dihydropurin-8-yl)benzenesulfonic acid
• CAS No.: 152529-79-8
• Molecular Formula: C14H14N4O5S
• Molecular Weight: 350.355
• DSSTox Substance ID: DTXSID80415532
• Nikkaji Number: J568.304A
• Wikidata: Q27088472
• Pharos Ligand ID: 1RV5LVQQ661T
• ChEMBL ID: CHEMBL8565
• Mol file: 152529-79-8.mol

Synonyms:1-propyl-8-(4-sulfophenyl)xanthine;1-propyl-8-p-sulfophenylxanthine;PSB 1115;PSB-1115;PSB1115

Chemical Property of 4-(2,6-Dioxo-1-propyl-3,7-dihydropurin-8-yl)benzenesulfonic acid

Chemical Property:

• Melting Point: >300 °C
• PKA: -1.59±0.50(Predicted)
• PSA: 146.29000
• Density: 1.522±0.06 g/cm3(Predicted)
• LogP: 1.81740
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 350.06849073
• Heavy Atom Count: 24
• Complexity: 611

Purity/Quality:

98%min ^*data from raw suppliers

4-(2,6-Dioxo-1-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)benzenesulfonicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCN1C(=O)C2=C(NC1=O)N=C(N2)C3=CC=C(C=C3)S(=O)(=O)O

Technology Process of 4-(2,6-Dioxo-1-propyl-3,7-dihydropurin-8-yl)benzenesulfonic acid

There total 9 articles about 4-(2,6-Dioxo-1-propyl-3,7-dihydropurin-8-yl)benzenesulfonic acid 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: 86.0%

6-amino-3-propyl-5-(4-sulfophenyl)carboxamidouracil (152529-72-1) → 4-(2,3,6,7-tetrahydro-2,6-dioxo-1-propyl-1H-purin-8-yl)benzenesulfonic acid (152529-79-8)

Guidance literature:

With polyphosphoric acid trimethylsilyl ester; for 1h; Heating;

DOI:10.1021/jm00074a015

Reference yield:

4-(2,6-dioxo-1-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-benzenesulfonic acid 3-nitro-phenyl ester (666716-03-6) → meta-nitrophenol (554-84-7) + 4-(2,3,6,7-tetrahydro-2,6-dioxo-1-propyl-1H-purin-8-yl)benzenesulfonic acid (152529-79-8)

Guidance literature:

With sodium hydroxide; In dimethyl sulfoxide; at 37 ℃; Equilibrium constant;

DOI:10.1021/jm0310030

Reference yield:

5,6-diamino-3-propyluracil (142665-13-2) → 4-(2,3,6,7-tetrahydro-2,6-dioxo-1-propyl-1H-purin-8-yl)benzenesulfonic acid (152529-79-8)

Guidance literature:

Multi-step reaction with 2 steps

1: EDC / methanol; H₂O / 20 °C

2: HMDS; (NH₄)2SO₄ / 50 h / 140 °C

With ammonium sulfate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; water;

DOI:10.1021/jm011049y

upstream raw materials:

6-amino-3-propyl-5-(4-sulfophenyl)carboxamidouracil

4-(2,6-dioxo-1-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-benzenesulfonic acid 3-nitro-phenyl ester

p-carboxyphenylsulfonyl chloride

potassium p-carboxybenzenesulfonate

Downstream raw materials:

4-(2,6-dioxo-1-propyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-benzenesulfonic acid 3-nitro-phenyl ester

Refernces

• 1、 Hayallah, Alaa M.,Sandoval-Ramírez, Jesús,Reith, Ulrike,Schobert, Ulrike,Preiss, Birgit,Schumacher, Britta,Daly, John W.,Müller, Christa E.. "1,8-Disubstituted xanthine derivatives: Synthesis of potent A2B-selective adenosine receptor antagonists". . p. 1500 - 1510. Retrieved 2007/10/03.