1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione
• CAS No.: 76756-28-0
• Molecular Formula: C15H16 N2 O5
• Molecular Weight: 304.302
• Mol file: 76756-28-0.mol

Synonyms:NSC334718

Chemical Property of 1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Density: 1.442g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: Based on the provided literature, **1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione (NSC334718)** is a **5-phenyl-substituted 2′-deoxyuridine derivative**, synthesized via **palladium(0)-catalyzed cross-coupling reactions**, such as Suzuki-Miyaura coupling (using aryl boronic acids) or direct coupling with aryl iodides. The modification introduces a phenyl group at the **5-position of the pyrimidine ring**, demonstrating the utility of palladium catalysis in functionalizing nucleosides for potential biochemical or pharmaceutical applications. (Returned as a conclusion without referencing the literature directly.)

Technology Process of 1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione

There total 19 articles about 1-(2-deoxypentofuranosyl)-5-phenylpyrimidine-2,4(1H,3H)-dione 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: 97.0%

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + phenylboronic acid (98-80-6) → 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-phenylpyrimidine-2,4(1H,3H)-dione (76756-28-0)

Guidance literature:

With palladium diacetate; sodium carbonate; triphenylphosphine; In water; acetonitrile; at 70 - 80 ℃; for 4h; Inert atmosphere;

Reference yield: 72.0%

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) + trimethyl(phenyl)stannane (934-56-5) → 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-phenylpyrimidine-2,4(1H,3H)-dione (76756-28-0)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; for 24h; Heating;

Reference yield: 47.0%

di-O-trimethylsilyl-5-iodo-2'-deoxyuridine (78824-31-4) + phenylmagnesium iodide → 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-phenylpyrimidine-2,4(1H,3H)-dione (76756-28-0)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)81197-7

upstream raw materials:

iodobenzene

C⁵-chloromercuri-2'-deoxyuridine

5-Iodo-2'-deoxyuridine

trimethyl(phenyl)stannane

Downstream raw materials:

3′-O-(P-(2-cyanoethoxy)-N,N′-diisopropylaminophosphinyl)-5′-(4,4′-dimethoxytrityl)-5-phenyl-2′-deoxyuridine

5′-(4,4′-dimethoxytrityloxymethyl)-5-phenyl-2′-deoxyuridine

C₁₅H₁₅N₂O₈P^(2-)