2,8-Dimercapto-5-(4-nitro-phenyl)-5H-pyrano(2,3-d;6,5-d)dipyrimidine-4,6-diol

Base Information

• Chemical Name: 2,8-Dimercapto-5-(4-nitro-phenyl)-5H-pyrano(2,3-d;6,5-d)dipyrimidine-4,6-diol
• CAS No.: 223393-69-9
• Molecular Formula: C₁₅H₉N₅O₅S₂
• Molecular Weight: 403.399
• NSC Number: 705851
• UNII: Q7D7PQV7A8
• DSSTox Substance ID: DTXSID90944989
• ChEMBL ID: CHEMBL178865
• Mol file: 223393-69-9.mol

Synonyms:V-165;223393-69-9;V 165;Q7D7PQV7A8;UNII-Q7D7PQV7A8;2,8-Dimercapto-5-(4-nitro-phenyl)-5H-pyrano(2,3-d;6,5-d)dipyrimidine-4,6-diol;CHEMBL178865;5-(4-nitrophenyl)-2,8-dithioxo-5,7,8,9-tetrahydro-2H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(1H,3H)-dione;NSC705851;D07ECH;SCHEMBL13788910;DTXSID90944989;BDBM50476419;STL150551;STL349538;AKOS005750605;AKOS022142146;AKOS040754311;NSC-705851;NCI60_037697;4-(4-nitrophenyl)-2,2-bis(sulfanyl)[?]-4,4-diol;2,8-Dimercapto-5-(4-nitro-phenyl)-5H-pyrano[2,3-d;2,8-dimercapto-5-(4-nitrophenyl)-5h-pyrano[2,3-d:6,5-d']dipyrimidine-4,6-diol;5-(4-Nitrophenyl)-2,8-bis(sulfanyl)-5H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6-diol;5-(4-nitrophenyl)-2,8-disulfanyl-5H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6-diol;2H-PYRANO(2,3-D:6,5-D')DIPYRIMIDINE-4,6(1H,3H)-DIONE, 5,7,8,9-TETRAHYDRO-5-(4-NITROPHENYL)-2,8-DITHIOXO-;5,7,8,9-TETRAHYDRO-5-(4-NITROPHENYL)-2,8-DITHIOXO-2H-PYRANO(2,3-D:6,5-D')DIPYRIMIDINE-4,6(1H,3H)-DIONE;9-(4-Nitrophenyl)-5,13-bis(sulfanylidene)-2-oxa-4,6,12,14-tetrazatricyclo[8.4.0.03,8]tetradeca-1(10),3(8)-diene-7,11-dione

Chemical Property of 2,8-Dimercapto-5-(4-nitro-phenyl)-5H-pyrano(2,3-d;6,5-d)dipyrimidine-4,6-diol

Chemical Property:

• Density: 1.83±0.1 g/cm3(Predicted)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 403.00451075
• Heavy Atom Count: 27
• Complexity: 801

Purity/Quality:

5-(4-NITROPHENYL)-4,6-DIHYDROXY-2,8-DISULFANYL-5H-PYRANO[2,3-D:6,5-D]DIPYRIMIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2C3=C(NC(=S)NC3=O)OC4=C2C(=O)NC(=S)N4)[N+](=O)[O-]

Technology Process of 2,8-Dimercapto-5-(4-nitro-phenyl)-5H-pyrano(2,3-d;6,5-d)dipyrimidine-4,6-diol

There total 4 articles about 2,8-Dimercapto-5-(4-nitro-phenyl)-5H-pyrano(2,3-d;6,5-d)dipyrimidine-4,6-diol 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: 91.0%

5,5'-(4-nitrophenylmethylene)bis(2-thiobarbituric acid), pyridinium salt → 5-(4-nitrophenyl)-2,8-dithioxo-5,7,8,9-tetrahydro-2H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(1H,3H)-dione (223393-69-9)

Guidance literature:

With trifluoroacetic anhydride; at 30 - 40 ℃; for 3h;

Reference yield: 72.0%

4,6-dihydroxy-2-mercaptopyrimidine (504-17-6,157796-99-1,924832-30-4) + 4-nitrobenzaldehdye (555-16-8) → 5-(4-nitrophenyl)-2,8-dithioxo-5,7,8,9-tetrahydro-2H-pyrano[2,3-d:6,5-d']dipyrimidine-4,6(1H,3H)-dione (223393-69-9)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; at 80 ℃; for 5.33333h; regioselective reaction;

DOI:10.1002/jhet.2165

Reference yield:

C5H5N*C15H11N5O6S2 → 4-chlorine-6-hydroxy-5-(4-nitrophenyl)-5,9-dihydro-1H-pyrano[2,3-d;6,5-d']dipyrimidine-2,8-dithione (844865-01-6) + 4,6-dihydroxy-5,9-dihydro-5-(4-nitrophenyl)-1H-pyrano[2,3-d;6,5-d']dipyrimidine-2,8-dithione (223393-69-9)

Guidance literature:

With trichlorophosphate; for 0.666667 - 0.833333h; Heating / reflux;

upstream raw materials:

4,6-dihydroxy-2-mercaptopyrimidine

4-nitrobenzaldehdye