6-(4-Chloro-phenyl)-1-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-1,6-dihydro-pyrazolo(4,3-d)pyrimidin-7-one

Base Information

• Chemical Name: 6-(4-Chloro-phenyl)-1-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-1,6-dihydro-pyrazolo(4,3-d)pyrimidin-7-one
• CAS No.: 89889-80-5
• Molecular Formula: C17H17ClN4O5
• Molecular Weight: 392.7937
• DSSTox Substance ID: DTXSID30237928
• Wikidata: Q83120199
• ChEMBL ID: CHEMBL4205743
• Mol file: 89889-80-5.mol

Synonyms:89889-80-5;6-(4-Chloro-phenyl)-1-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-1,6-dihydro-pyrazolo(4,3-d)pyrimidin-7-one;6-(4-Chloro-phenyl)-1-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one;CHEMBL4205743;DTXSID30237928;6-(4-chlorophenyl)-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-3-methyl-pyrazolo[4,3-d]pyrimidin-7-one

Chemical Property of 6-(4-Chloro-phenyl)-1-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-1,6-dihydro-pyrazolo(4,3-d)pyrimidin-7-one

Chemical Property:

• Vapor Pressure: 1.22E-21mmHg at 25°C
• Boiling Point: 718.1°C at 760 mmHg
• Flash Point: 388.1°C
• Density: 1.72g/cm³
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 392.0887473
• Heavy Atom Count: 27
• Complexity: 602

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NN(C2=C1N=CN(C2=O)C3=CC=C(C=C3)Cl)C4C(C(C(O4)CO)O)O
• Isomeric SMILES: CC1=NN(C2=C1N=CN(C2=O)C3=CC=C(C=C3)Cl)[C@H]4[C@@H]([C@@H]([C@H](O4)CO)O)O

Technology Process of 6-(4-Chloro-phenyl)-1-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-1,6-dihydro-pyrazolo(4,3-d)pyrimidin-7-one

There total 7 articles about 6-(4-Chloro-phenyl)-1-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-1,6-dihydro-pyrazolo(4,3-d)pyrimidin-7-one 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: 82.0%

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(4-chloro-phenyl)-3-methyl-7-oxo-6,7-dihydro-pyrazolo[4,3-d]pyrimidin-1-yl]-tetrahydro-furan-3-yl ester (89889-72-5) → 6-(4-Chloro-phenyl)-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one (89889-80-5)

Guidance literature:

With ammonia; at 0 ℃; for 18h;

DOI:10.1021/jm00374a009

Reference yield:

2,7-dimethyl-3,8-dinitrodipyrazolo[1,5-a;1',5'-d]pyrazine-4,9-dione (80030-73-5) → 6-(4-Chloro-phenyl)-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one (89889-80-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / dioxane / Ambient temperature

2: 72 percent / aq. NaBH₄ / 10percent Pd/C / methanol / 3 h

3: 62 percent / 5 h / 180 °C

4: (NH₄)2SO₄ / 8 h / Heating

5: SnCl₄ / acetonitrile / 18 h / 25 °C

6: 82 percent / methanolic NH₃ / 18 h / 0 °C

With ammonium sulfate; sodium tetrahydroborate; ammonia; tin(IV) chloride; palladium on activated charcoal; In 1,4-dioxane; methanol; acetonitrile;

DOI:10.1021/jm00374a009

Reference yield:

4-chloro-aniline (106-47-8) → 6-(4-Chloro-phenyl)-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-3-methyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one (89889-80-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / dioxane / Ambient temperature

2: 72 percent / aq. NaBH₄ / 10percent Pd/C / methanol / 3 h

3: 62 percent / 5 h / 180 °C

4: (NH₄)2SO₄ / 8 h / Heating

5: SnCl₄ / acetonitrile / 18 h / 25 °C

6: 82 percent / methanolic NH₃ / 18 h / 0 °C

With ammonium sulfate; sodium tetrahydroborate; ammonia; tin(IV) chloride; palladium on activated charcoal; In 1,4-dioxane; methanol; acetonitrile;

DOI:10.1021/jm00374a009

upstream raw materials:

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(4-chloro-phenyl)-3-methyl-7-oxo-6,7-dihydro-pyrazolo[4,3-d]pyrimidin-1-yl]-tetrahydro-furan-3-yl ester

2,7-dimethyl-3,8-dinitrodipyrazolo[1,5-a;1',5'-d]pyrazine-4,9-dione

4-chloro-aniline

4-Amino-5-methyl-2H-pyrazole-3-carboxylic acid (4-chloro-phenyl)-amide