1-(BETA-D-2-DEOXYRIBOFURANOSYL)-4-(1,2,4-TRIAZOL-1-YL)-5-METHYLPYRIMIDIN-2-ONE

Base Information

• Chemical Name: 1-(BETA-D-2-DEOXYRIBOFURANOSYL)-4-(1,2,4-TRIAZOL-1-YL)-5-METHYLPYRIMIDIN-2-ONE
• CAS No.: 109389-24-4
• Molecular Formula: C₁₁H₁₃N₅O₄
• Molecular Weight: 279.255
• Mol file: 109389-24-4.mol

Synonyms:1-(BETA-D-2-DEOXYRIBOFURANOSYL)-4-(1,2,4-TRIAZOL-1-YL)-5-METHYLPYRIMIDIN-2-ONE

Chemical Property of 1-(BETA-D-2-DEOXYRIBOFURANOSYL)-4-(1,2,4-TRIAZOL-1-YL)-5-METHYLPYRIMIDIN-2-ONE

Chemical Property:

• PSA: 115.29000
• LogP: -1.22690

Purity/Quality:

97% ^*data from raw suppliers

1-(β-D-2-Deoxyribofuranosyl)-4-(1,2,4-triazol-1-yl)pyrimidin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-(β-D-2-Deoxyribofuranosyl)-4-(1,2,4-triazol-1-yl)pyrimidin-2-one displayed anti-HIV activities. Used as a reagent to synthesize adducts of deoxyadenosine (M1A) and deoxycytidine (M1C).

Technology Process of 1-(BETA-D-2-DEOXYRIBOFURANOSYL)-4-(1,2,4-TRIAZOL-1-YL)-5-METHYLPYRIMIDIN-2-ONE

There total 4 articles about 1-(BETA-D-2-DEOXYRIBOFURANOSYL)-4-(1,2,4-TRIAZOL-1-YL)-5-METHYLPYRIMIDIN-2-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: 79.0%

1,2,4-Triazole (288-88-0) + 2'-deoxyuridine (951-78-0,63844-76-8) → 1-(2-Deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidinone (109389-24-4)

Guidance literature:

With trifluoroacetic anhydride;

DOI:10.1016/0040-4039(95)00587-3

Reference yield:

Trifluoro-acetic acid (2R,3S,5R)-5-(2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-2-(2,2,2-trifluoro-acetoxymethyl)-tetrahydro-furan-3-yl ester → 1-(2-Deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidinone (109389-24-4)

Guidance literature:

With silica gel; In methanol; dichloromethane;

DOI:10.1016/S0014-827X(98)00107-4

Reference yield:

2'-deoxyuridine (951-78-0,63844-76-8) → 1-(2-Deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidinone (109389-24-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 24 h / 20 °C

2: pyridine / 72 h / 20 °C

3: silica gel / methanol; CH₂Cl₂

With pyridine; silica gel; In methanol; dichloromethane; 1: Acylation / 2: Substitution / 3: deacylation;

DOI:10.1016/S0014-827X(98)00107-4

upstream raw materials:

1,2,4-Triazole

2'-deoxyuridine

Downstream raw materials:

N⁴-ureidocarbonyl-5'-O-di(p-anisyl)phenylmethyl-2'-deoxycytidine

1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-4-[1,2,4]triazol-1-yl-1H-pyrimidin-2-one