5-(4-Fluoro-phenylethynyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 5-(4-Fluoro-phenylethynyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
• CAS No.: 151362-02-6
• Molecular Formula: C₁₇H₁₅FN₂O₅
• Molecular Weight: 346.315
• Mol file: 151362-02-6.mol

Synonyms:5-(4-Fluoro-phenylethynyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Chemical Property of 5-(4-Fluoro-phenylethynyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(4-Fluoro-phenylethynyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione

There total 4 articles about 5-(4-Fluoro-phenylethynyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-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: 76.0%

1-ethynyl-4-fluorobenzene (766-98-3) + 5-(Trifluoromethanesulfonyloxy)-2'-deoxyuridine (151361-85-2) → 3-(2′-deoxy-β-D-ribofuranosyl)-6-(4-fluorophenyl)-2,3-dihydrofuro-[2,3-d]pyrimidin-2-one + 5-(4-Fluoro-phenylethynyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione (151362-02-6)

Guidance literature:

With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 40 ℃; for 4h;

DOI:10.1021/jo00076a019

Reference yield:

5-hydroxy-2'-deoxyuridine (5168-36-5,13011-49-9) → 5-(4-Fluoro-phenylethynyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione (151362-02-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / K₂CO₃ / H₂O; dioxane

2: 76 percent / Et₃N, copper(I) iodide / Pd(PPh₃)4 / dimethylformamide / 4 h / 40 °C

With copper(l) iodide; potassium carbonate; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00076a019

Reference yield:

1-(4-fluorophenyl)-2-trimethylsilylacetylene (130995-12-9) → 5-(4-Fluoro-phenylethynyl)-1-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione (151362-02-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / KOH / methanol / 1 h / Ambient temperature

2: 76 percent / Et₃N, copper(I) iodide / Pd(PPh₃)4 / dimethylformamide / 4 h / 40 °C

With potassium hydroxide; copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo00076a019

upstream raw materials:

1-ethynyl-4-fluorobenzene

5-(Trifluoromethanesulfonyloxy)-2'-deoxyuridine

5-hydroxy-2'-deoxyuridine

1-(4-fluorophenyl)-2-trimethylsilylacetylene