6-Phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Base Information

• Chemical Name: 6-Phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine
• CAS No.: 175787-78-7
• Molecular Formula: C16H16N4O
• Molecular Weight: 280.329
• DSSTox Substance ID: DTXSID30570908
• Nikkaji Number: J1.131.074E
• Mol file: 175787-78-7.mol

Synonyms:6-Phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine;175787-78-7;9-(Oxan-2-yl)-6-phenyl-9H-purine;9-(oxan-2-yl)-6-phenylpurine;DTXSID30570908;AKOS015905113;6-phenyl-9-tetrahydro-2H-pyran-2-yl-9H-purine

Chemical Property of 6-Phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 280.13241115
• Heavy Atom Count: 21
• Complexity: 347

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCOC(C1)N2C=NC3=C(N=CN=C32)C4=CC=CC=C4

Technology Process of 6-Phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

There total 6 articles about 6-Phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 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: 95.0%

6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (7306-68-5) + phenylboronic acid (98-80-6) → 6-phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (175787-78-7)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 100 ℃;

DOI:10.1055/s-1999-2753

Reference yield: 10.0%

phenylmagnesium bromide (100-58-3) + 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (7306-68-5) → 6-phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (175787-78-7)

Guidance literature:

With copper(l) iodide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 2h; then overnight at room temperature;

DOI:10.1016/0040-4039(95)02375-5

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → 6-phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (175787-78-7)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / tetrahydrofuran / 15 h / Reflux

2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 12 h / Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; toluene; 2: |Suzuki Coupling;

DOI:10.17344/acsi.2017.3419

upstream raw materials:

phenylmagnesium bromide

6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

phenylboronic acid

6-chloropurine

Downstream raw materials:

3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)benzaldehyde

9-[2-deoxy-3,5-di-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-phenylpurine

6-phenyl-9H-purine