Pyrimidine-5-carboxaldehyde

Base Information

• Chemical Name: Pyrimidine-5-carboxaldehyde
• CAS No.: 10070-92-5
• Molecular Formula: C5H4N2O
• Molecular Weight: 108.1
• Hs Code.: 2933599090
• European Community (EC) Number: 631-168-9
• DSSTox Substance ID: DTXSID10375493
• Nikkaji Number: J570.819B
• Wikidata: Q72504824
• ChEMBL ID: CHEMBL4466138
• Mol file: 10070-92-5.mol

Synonyms:5-Formylpyrimidine;5-Pyrimidinecarboxaldehyde;

Chemical Property of Pyrimidine-5-carboxaldehyde

Chemical Property:

• Vapor Pressure: 0.0869mmHg at 25°C
• Melting Point: 39-43 °C
• Refractive Index: 1.581
• Boiling Point: 225.3 °C at 760 mmHg
• PKA: 1.15±0.10(Predicted)
• Flash Point: 92.6 °C
• PSA: 42.85000
• Density: 1.234 g/cm³
• LogP: 0.28910
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 108.032362755
• Heavy Atom Count: 8
• Complexity: 78.5

Purity/Quality:

99% ^*data from raw suppliers

5-Pyrimidinecarboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-43-22
• Safety Statements: 26-36/37/39-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=NC=N1)C=O
• Uses: Pyrimidine-5-carboxaldehyde is used in the preparation of (S)- and (R)-pyrimidyl alkanol by reacting with diisopropylzinc and (n-butyl)ethyl(n-hexyl)(n-propyl)methane.

Technology Process of Pyrimidine-5-carboxaldehyde

There total 10 articles about Pyrimidine-5-carboxaldehyde 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: 95.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → pyrimidine-5-carbaldehyde (10070-92-5)

Guidance literature:

N,N-dimethyl-formamide; With aluminum (III) chloride; trichlorophosphate; at 5 ℃; for 0.5h;

uracil; at 5 ℃; for 2h; Temperature; Reagent/catalyst;

Reference yield: 52.0%

5-bromopyrimidine (4595-59-9) + formic acid ethyl ester (109-94-4) → pyrimidine-5-carbaldehyde (10070-92-5)

Guidance literature:

5-bromopyrimidine; With n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃; for 0.333333h;

formic acid ethyl ester; In tetrahydrofuran; hexane; at -100 ℃; for 0.333333h;

DOI:10.1021/jm049874c

Reference yield: 51.0%

5-bromopyrimidine (4595-59-9) + 2,2-diethoxy acetic acid (20461-86-3) → pyrimidine-5-carbaldehyde (10070-92-5)

Guidance literature:

With nickel(II) chloride hexahydrate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;

DOI:10.1002/anie.201610108

upstream raw materials:

5-bromopyrimidine

formic acid ethyl ester

N,N-dimethyl-formamide

3-Bromopyridine

Downstream raw materials:

5-(hydroxymethyl)pyrimidine

N-[(5-pyrimidinyl)methyl]-2-pyridinamine

3-(4'-cyano-5,2'-dimethyl[1,1'-biphenyl]-3-yl)-2-hydroxy-4-oxo-1-(5-pyrimidinylmethyl)-4H-pyrido[1,2-a]pyrimidinium inner salt

3,4-dihydro-2,4-dioxo-1-(pyrimidin-5-ylmethyl)-3-(α,α,α-trifluoro-m-tolyl)-2H-pyrido[1,2-a]pyrimidin-1-ium-3-ide

Refernces

• 1、 Huang, He,Li, Xiangmin,Yu, Chenguang,Zhang, Yueteng,Mariano, Patrick S.,Wang, Wei. "Visible-Light-Promoted Nickel- and Organic-Dye-Cocatalyzed Formylation Reaction of Aryl Halides and Triflates and Vinyl Bromides with Diethoxyacetic Acid as a Formyl Equivalent". . p. 1500 - 1505. Retrieved 2017.
• 2、 Coleman, Paul J,Brashear, Karen M,Askew, Ben C,Hutchinson, John H,McVean, Carol A,Duong,Feuston, Bradley P,Fernandez-Metzler, Carmen,Gentile, Michael A,Hartman, George D,Kimmel, Donald B,Leu, Chih-Tai,Lipfert, Lorraine,Merkle, Kara,Pennypacker, Brenda,Prueksaritanont, Thomayant,Rodan, Gideon A,Wesolowski, Gregg A,Rodan, Sevgi B,Duggan, Mark E. "Nonpeptide alphavbeta3 antagonists. Part 11: discovery and preclinical evaluation of potent alphavbeta3 antagonists for the prevention and treatment of osteoporosis.". . p. 4829 - 4837. Retrieved 2004.
• 3、 Hone, Christopher A.,Lopatka, Pavol,Munday, Rachel,O'Kearney-McMullan, Anne,Kappe, C. Oliver. "Continuous-flow Synthesis of Aryl Aldehydes by Pd-catalyzed Formylation of Aryl Bromides Using Carbon Monoxide and Hydrogen". . p. 326 - 337. Retrieved 2018/11/23.