2(1H)-Pyrimidinone, 1-(2-deoxy-b-D-erythro-pentofuranosyl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)

Base Information

• Chemical Name: 2(1H)-Pyrimidinone, 1-(2-deoxy-b-D-erythro-pentofuranosyl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)
• CAS No.: 109389-25-5
• Molecular Formula: C12H15 N5 O4
• Molecular Weight: 293.282
• Mol file: 109389-25-5.mol

Synonyms:2(1H)-Pyrimidinone, 1-(2-deoxy-b-D-erythro-pentofuranosyl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)

Chemical Property of 2(1H)-Pyrimidinone, 1-(2-deoxy-b-D-erythro-pentofuranosyl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)

Chemical Property:

• Vapor Pressure: 1.8E-16mmHg at 25°C
• Boiling Point: 624.7°Cat760mmHg
• Flash Point: 331.6°C
• PSA: 115.29000
• Density: 1.69g/cm³
• LogP: -1.22690

Purity/Quality:

97% ^*data from raw suppliers

2(1H)-PYRIMIDINONE, 1-(2-DEOXY-B-D-ERYTHRO-PENTOFURANOSYL)-5-METHYL-4-(1H-1,2,4-TRIAZOL-1-YL) 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2(1H)-Pyrimidinone, 1-(2-deoxy-b-D-erythro-pentofuranosyl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)

There total 6 articles about 2(1H)-Pyrimidinone, 1-(2-deoxy-b-D-erythro-pentofuranosyl)-5-methyl-4-(1H-1,2,4-triazol-1-yl) 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: 88.0%

1,2,3-triazole (288-36-8) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one (109389-25-5)

Guidance literature:

thymidine; With chloro-trimethyl-silane; triethylamine; In acetonitrile; at 20 ℃; for 1.5h;

1,2,3-triazole; With trichlorophosphate; In acetonitrile; at 0 ℃; for 5h;

With acetic acid; In methanol; at 20 ℃; for 4.5h;

DOI:10.1016/j.ejmech.2014.02.011

Reference yield: 81.2%

1,2,4-Triazole (288-88-0) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one (109389-25-5)

Guidance literature:

thymidine; With chloro-trimethyl-silane; triethylamine; In acetonitrile; at 23 ℃; for 2h;

1,2,4-Triazole; With trichlorophosphate; at 0 - 23 ℃; for 6h;

With acetic acid; In methanol; at 23 ℃; for 4.5h;

DOI:10.1002/anie.202002751

Reference yield:

thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4) → 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one (109389-25-5)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; acetonitrile / 1.5 h / Ambient temperature; other reagent

2: POCl₃ / acetonitrile / 5 h / 0 °C

3: 1.30 g / acetic acid; methanol / 4.5 h / Ambient temperature

With trichlorophosphate; In methanol; acetic acid; triethylamine; acetonitrile;

DOI:10.1080/07328319708002521

upstream raw materials:

1,2,4-Triazole

thymidine

3',5'-bis-O-(trimethylsilyl)-thymidine

1,2,3-triazole

Downstream raw materials:

N,5-dimethyl-2’-deoxycytidine

3′,5′-di-O-trityl-thymidine

O⁴-methyl thymidine

1-(2'-deoxy-5'-O-dimethoxytrityl-β-D-ribofuranosyl)-5-methyl-4-(1,2,4-triazol-1-yl)-2-pyrimidone

Refernces

• 1、 Saudi, Milind,Zmurko, Joanna,Kaptein, Suzanne,Rozenski, Jef,Neyts, Johan,Van Aerschot, Arthur. "In search of Flavivirus inhibitors part 2: Tritylated, diphenylmethylated and other alkylated nucleoside analogues". . p. 98 - 109. Retrieved 2014/03/21.
• 2、 Jones,Sayers,Walker,De Clercq. "Synthesis and antiviral properties of (E)-5-(2-bromovinyl)-2'-deoxycytidine-related compounds". . p. 268 - 271. Retrieved 2007/10/02.