N(4)-methyl-5-azacytidine

Base Information

• Chemical Name: N(4)-methyl-5-azacytidine
• CAS No.: 27826-76-2
• Molecular Formula: C₉H₁₄N₄O₅
• Molecular Weight: 258.234
• Mol file: 27826-76-2.mol

Synonyms:s-Triazin-2(1H)-one,4-(methylamino)-1-b-D-ribofuranosyl- (8CI); N4-Methyl-5-azacytidine

Chemical Property of N(4)-methyl-5-azacytidine

Chemical Property:

• Vapor Pressure: 1.02E-11mmHg at 25°C
• Boiling Point: 491.4°Cat760mmHg
• PKA: 13.46±0.70(Predicted)
• Flash Point: 251°C
• PSA: 129.73000
• Density: 1.84g/cm³
• LogP: -2.63550

Purity/Quality:

97% ^*data from raw suppliers

N4-METHYL-5-AZACYTIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N(4)-methyl-5-azacytidine

There total 8 articles about N(4)-methyl-5-azacytidine 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: 74.0%

N4-Methyl-2',3',5'-tri-O-benzoyl-β-D-5-azacytidine (211695-85-1) → 4-methylamino-1-β-D-ribofuranosyl-1H-[1,3,5]triazin-2-one (27826-76-2)

Guidance literature:

With sodium methylate; In methanol; 1.) r.t., 30 min, 2.) -20 deg C, overnight;

DOI:10.1135/cccc19980713

Reference yield: 64.0%

4-methoxy-1-β-D-ribofuranosyl-1H-[1,3,5]triazin-2-one (27826-75-1) + methylamine (74-89-5) → 4-methylamino-1-β-D-ribofuranosyl-1H-[1,3,5]triazin-2-one (27826-76-2)

Guidance literature:

In methanol; for 1.5h; Ambient temperature;

DOI:10.1135/cccc19980713

Reference yield:

2,3,5-tri-O-benzoyl-β-D-ribosyl isocyanate (21823-89-2) → 4-methylamino-1-β-D-ribofuranosyl-1H-[1,3,5]triazin-2-one (27826-76-2)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / 1.) MeOH, C₆H₆, 2.) r.t., 1 h

2: benzene / Ambient temperature

3: 74 percent / NaOMe / methanol / 1.) r.t., 30 min, 2.) -20 deg C, overnight

With sodium methylate; In methanol; benzene;

DOI:10.1135/cccc19980713

upstream raw materials:

4-methoxy-1-β-D-ribofuranosyl-1H-[1,3,5]triazin-2-one

methylamine

N⁴-Methyl-2',3',5'-tri-O-benzoyl-β-D-5-azacytidine

2,3,5-tri-O-benzoyl-β-D-ribosyl isocyanate

Refernces

Synthesis and biological activity of N⁴-methyl-5-azacytidines

10.1135/cccc19980713

The research focuses on the synthesis and biological activity of N4-methyl-5-azacytidine (1) and N4,N4-dimethyl-5-azacytidine (2), which are derivatives of 5-azacytidine, a compound used in the clinical treatment of acute leukemia and as a hypomethylating agent in molecular and cell biology. The study aimed to investigate the effects of N4-methyl and N4,N4-dimethyl substitutions on the biological activity of 5-azacytidine, including antibacterial, antitumor, and antiviral properties. The synthesis involved various chemical reactions using compounds such as benzoylated 4-methoxy-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, silylated N4-methyl- or N4,N4-dimethyl-5-azacytosines, and 2,3,5-tri-O-benzoyl-α,β-D-ribofuranosyl chloride. The researchers concluded that the nucleosides 1 and 2 exhibited lower antibacterial, antitumor, and antiviral activity compared to unsubstituted 5-azacytidine, likely due to the steric hindrance caused by the methyl groups preventing incorporation into nucleic acids. Key chemicals used in the synthesis process included various nucleoside derivatives, protecting groups, and reagents for aminolysis, glycosylation, and isocyanate reactions.