1-((2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-3-phenylurea

Base Information

• Chemical Name: 1-((2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-3-phenylurea
• CAS No.: 1222521-18-7
• Molecular Formula: C₁₇H₂₀N₄O₅
• Molecular Weight: 360.37
• Mol file: 1222521-18-7.mol

Synonyms:1-((2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-3-phenylurea

Chemical Property of 1-((2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-3-phenylurea

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-3-phenylurea

There total 5 articles about 1-((2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-3-phenylurea 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%

1-((2S,3S,5R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-3-phenylurea → 1-((2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-3-phenylurea (1222521-18-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.5b00327

Reference yield: 52.0%

3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2) + triethylamine carbonate (15715-58-9) + aniline (62-53-3) → 1-((2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-3-phenylurea (1222521-18-7)

Guidance literature:

With water; In 1,4-dioxane; at 40 ℃; for 48h;

DOI:10.1016/j.tet.2010.01.017

Reference yield:

3'-azido-2',3'-deoxythymidine (30516-87-1,399024-19-2) → 1-((2S,3S,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl)-3-phenylurea (1222521-18-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1H-imidazole / 12 h / 20 °C / Inert atmosphere

2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr / Inert atmosphere

3: dichloromethane / 0 - 20 °C / Inert atmosphere

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

With 1H-imidazole; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/acs.jmedchem.5b00327

upstream raw materials:

3'-azido-2',3'-deoxythymidine

triethylamine carbonate

aniline

1-{(2R,4S,5S)-4-azido-5-{{[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl}tetrahydrofuran-2-yl}-5-methylpyrimidine-2,4(1H,3H)-dione