4-Amino-2-hydroxypyrimidine-5-carbonitrile

Base Information

• Chemical Name: 4-Amino-2-hydroxypyrimidine-5-carbonitrile
• CAS No.: 16462-28-5
• Molecular Formula: C₅H₄N₄O
• Molecular Weight: 136.113
• Hs Code.: 2933599090
• DSSTox Substance ID: DTXSID90358683
• Wikidata: Q82139439
• Mol file: 16462-28-5.mol

Synonyms:16462-28-5;4-amino-2-hydroxypyrimidine-5-carbonitrile;4-amino-2-oxo-1,2-dihydropyrimidine-5-carbonitrile;6-amino-2-oxo-1H-pyrimidine-5-carbonitrile;4-Amino-2-oxo-1,2-dihydro-5-pyrimidinecarbonitrile;6-amino-2-oxo-1,2-dihydropyrimidine-5-carbonitrile;4-Amino-2-oxo-1,2-dihydro-pyrimidine-5-carbonitrile;5-Pyrimidinecarbonitrile, 4-amino-1,2-dihydro-2-oxo- (9CI);5-cyanocytosine;EC-000.1627;SCHEMBL3825045;DTXSID90358683;KFDKBQHGALFUAJ-UHFFFAOYSA-N;BBL012794;MFCD00767571;MFCD09863919;STK784021;STK935569;AKOS002664606;AKOS005665306;AKOS015902256;SB57496;SY263317;VS-03520;FT-0750171;EN300-102897;F17272;5-Pyrimidinecarbonitrile, 4-amino-1,2-dihydro-2-oxo-;F1918-0073

Chemical Property of 4-Amino-2-hydroxypyrimidine-5-carbonitrile

Chemical Property:

• Melting Point: 270 °C (decomp)
• Boiling Point: °Cat760mmHg
• PKA: 6.95±0.10(Predicted)
• Flash Point: °C
• PSA: 96.55000
• Density: 1.6g/cm³
• LogP: -0.43382
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 136.03851076
• Heavy Atom Count: 10
• Complexity: 279

Purity/Quality:

98%min ^*data from raw suppliers

4-amino-2-oxo-1,2-dihydropyrimidine-5-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=O)NC(=C1C#N)N

Technology Process of 4-Amino-2-hydroxypyrimidine-5-carbonitrile

There total 7 articles about 4-Amino-2-hydroxypyrimidine-5-carbonitrile 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: 41.0%

(2,2-dicyano-vinyl)-urea (14048-06-7) → 5-cyanocytosine (16462-28-5)

Guidance literature:

(2,2-dicyano-vinyl)-urea; With sodium methylate;

With acetic acid;

DOI:10.1021/jo401684j

Reference yield:

4-Amino-2-bromo-5-pyrimidinecarbonitrile (94741-70-5) → 4-Amino-2-ethoxy-pyrimidine-5-carbonitrile (94742-00-4) + 2-Hydroxy-4-amino-5-cyano-pyrimidin (16462-28-5)

Guidance literature:

With potassium hydroxide; Yield given. Multistep reaction. Yields of byproduct given; 1.) DMSO, EtOH, 15 min, 2.) 50 deg C, 1 h;

DOI:10.1055/s-1984-30931

Reference yield:

4-amino-2-(ethylthio)pyrimidine-5-carbonitrile (16462-29-6) → 5-cyanocytosine (16462-28-5)

Guidance literature:

With hydrogenchloride; water;

upstream raw materials:

4-amino-2-(ethylthio)pyrimidine-5-carbonitrile

urea

Ethoxymethylenemalononitrile

(2,2-dicyano-vinyl)-urea

Downstream raw materials:

5-cyanouracil

4-amino-2-oxo-1,2-dihydro-pyrimidine-5-carboxylic acid amide

4-amino-5-aminomethyl-1H-pyrimidin-2-one

Refernces

• 1、 -. "A microwave-assisted high-efficient synthetic 5-cyanogenetic uracil method". Paragraph 0023; 0025. . Retrieved 2020/02/08.