N4-Acetylcytosine

Base Information

• Chemical Name: N4-Acetylcytosine
• CAS No.: 14631-20-0
• Molecular Formula: C6H7N3O2
• Molecular Weight: 153.14
• Hs Code.: DERIVATION
• European Community (EC) Number: 619-683-7
• NSC Number: 210403
• DSSTox Substance ID: DTXSID30163354
• Nikkaji Number: J152.171C
• Wikidata: Q20892014
• ChEMBL ID: CHEMBL3273673
• Mol file: 14631-20-0.mol

Synonyms:N4-Acetylcytosine;14631-20-0;N-Acetylcytosine;N-(2-Oxo-1,2-dihydropyrimidin-4-yl)acetamide;N4 -acetylcytosine;N-(2-oxo-1H-pyrimidin-6-yl)acetamide;n(4)-acetylcytosine;Acetamide, N-(1,2-dihydro-2-oxo-4-pyrimidinyl)-;MFCD00134466;4-acetylamino-1,2-dihydro-2-pyrimidone;N-acetyl cytosine;NSC210403;N-(2-hydroxypyrimidin-4-yl)acetamide;N4-Acetylcytosine, 99%;N-(2-Oxo-1,2-dihydro-4-pyrimidinyl)acetamide;SCHEMBL21187;CHEMBL3273673;IJCKBIINTQEGLY-UHFFFAOYSA-;DTXSID30163354;CHEBI:146134;IJCKBIINTQEGLY-UHFFFAOYSA-N;AMY23360;BCP12969;4-(acetylamino)pyrimidine-2(1H)-one;AKOS006227633;AKOS015837993;AKOS022634962;AC-8695;CS-W010939;NSC 210403;NSC-210403;N-(2-oxo-3H-pyrimidin-4-yl)acetamide;AS-12395;SY069214;FT-0604353;F16463;N-(1,2-dihydro-2-oxo-4-pyrimidinyl)acetamide;EN300-6808778;W-201296;Q20892014;InChI=1/C6H7N3O2/c1-4(10)8-5-2-3-7-6(11)9-5/h2-3H,1H3,(H2,7,8,9,10,11)

Chemical Property of N4-Acetylcytosine

Chemical Property:

• Melting Point: >300 °C(lit.)
• Refractive Index: 1.625
• PKA: 7.60±0.10(Predicted)
• PSA: 75.11000
• Density: 1.41 g/cm³
• LogP: 0.21360
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Sparingly), Methanol (Very Slightly)
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 153.053826475
• Heavy Atom Count: 11
• Complexity: 255

Purity/Quality:

99% ^*data from raw suppliers

N4-Acetylcytosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26-37

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)NC1=CC=NC(=O)N1
• Uses: N4-Acetylcytosine may be used in the preparation of cytidine. It may be used in the preparation of 1-(4-azido-4-deoxy-β-D-glucopyranosyl)cytosine.

Technology Process of N4-Acetylcytosine

There total 9 articles about N4-Acetylcytosine 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: 98.0%

Cytosine (71-30-7) + acetic anhydride (108-24-7) → 4-N-Acetylcytosine (14631-20-0)

Guidance literature:

With phosphoric acid; at 100 ℃; for 8h;

Reference yield: 20.0%

4-Amino-1-(2,5-anhydro-β-D-arabinofuranosyl)pyrimidin-2(1H)-one (32830-01-6) → 4-N-Acetylcytosine (14631-20-0) + 4-Acetamido-1-(2,3-di-O-acetyl-5-bromo-5-deoxy-β-D-arabinofuranosyl)pyrimidin-2(1H)-one (84856-79-1) + 4-Amino-1-(5-bromo-5-deoxy-β-D-arabinofuranosyl)pyrimidin-2(1H)-one (58538-06-0)

Guidance literature:

With hydrogen bromide; In N,N-dimethyl-formamide; at 120 ℃; for 0.416667h;

Reference yield:

Cytosine (71-30-7) + acetyl chloride (75-36-5) → 4-N-Acetylcytosine (14631-20-0)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2019.01.027

upstream raw materials:

Cytosine

acetic anhydride

N-acetylcytidine

4-Amino-1-(2,5-anhydro-β-D-arabinofuranosyl)pyrimidin-2(1H)-one

Downstream raw materials:

N⁴-acetyl-2',3',5'-tri-O-benzoyl-2'-C-vinylcytidine

N⁴-acetyl-2',3',5'-tri-O-benzoyl-2'-C-[(trimethylsilyl)ethynyl]cytidine

cis-2-benzoyloxymethyl-4-(N₄'-acetylcytosin-1'-yl)-1,3-oxathiolane

Benzoic acid (2S,4S)-4-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-[1,3]dithiolan-2-ylmethyl ester

Refernces

• 1、 Codington et al.. "-". . p. 5164. Retrieved 1958.
• 2、 Routaboul, Christel,Norez, Caroline,Melin, Patricia,Molina, Marie-Carmen,Boucherle, Benjamin,Bossard, Florian,Noel, Sabrina,Robert, Renaud,Gauthier, Chantal,Becq, Frederic,Decout, Jean-Luc. "Discovery of α-aminoazaheterocycle-methylglyoxal adducts as a new class of high-affinity inhibitors of cystic fibrosis transmembrane conductance regulator chloride channels". . p. 1023 - 1035. Retrieved 2007.
• 3、 -. "Preparation method for synthesizing palbociclib intermediate and method for synthesizing palbociclib". Paragraph 0018. . Retrieved 2020/09/30.
• 4、 Krstulovi?, Luka,Safti?, Dijana,Ismaili, Hamit,Baji?, Miroslav,Glava?-Obrovac, Ljubica,?ini?, Biserka. "Synthesis and in vitro activity of N-sulfonylamidine-derived Pyrimidine Analogues". . p. 625 - 636. Retrieved 2018/05/07.