Ethyl 4-hydroxy-2-phenylpyrimidine-5-carboxylate

Base Information

• Chemical Name: Ethyl 4-hydroxy-2-phenylpyrimidine-5-carboxylate
• CAS No.: 55613-22-4
• Molecular Formula: C13H12 N2 O3
• Molecular Weight: 244.25
• Hs Code.: 2933599090
• DSSTox Substance ID: DTXSID70349690
• Nikkaji Number: J449.936K
• Wikidata: Q72475350
• ChEMBL ID: CHEMBL1343327
• Mol file: 55613-22-4.mol

Synonyms:Ethyl 4-hydroxy-2-phenylpyrimidine-5-carboxylate;55613-22-4;ETHYL 6-OXO-2-PHENYL-1,6-DIHYDRO-5-PYRIMIDINECARBOXYLATE;ethyl 6-oxo-2-phenyl-1,6-dihydropyrimidine-5-carboxylate;ethyl 6-oxo-2-phenyl-1H-pyrimidine-5-carboxylate;Ethyl 1,6-dihydro-6-oxo-2-phenylpyrimidine-5-carboxylate;SMR000059323;Oprea1_250176;MLS000038919;SCHEMBL2897245;CHEMBL1343327;DTXSID70349690;JSIHCFJCICVJHJ-UHFFFAOYSA-N;HMS1625K14;HMS2319A17;BCP27210;MFCD00695462;STK528900;AKOS001786114;AKOS005075618;SB58874;10M-541S;AM20040712;CS-0213093;FT-0640325;A15648;ethyl 2-phenyl-4-hydroxypyrimidine-5-carboxylate;J-521209;ethyl 3,4-dihydro-4-oxo-2-phenylpyrimidine-5-carboxylate;ethyl 4-oxo-2-phenyl-3,4-dihydropyrimidine-5-carboxylate

Chemical Property of Ethyl 4-hydroxy-2-phenylpyrimidine-5-carboxylate

Chemical Property:

• Vapor Pressure: 0.000358mmHg at 25°C
• Melting Point: 209-212oC
• Boiling Point: 309.1°Cat760mmHg
• Flash Point: 140.7°C
• PSA: 72.05000
• Density: 1.25g/cm³
• LogP: 1.61360
• Storage Temp.: 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 244.08479225
• Heavy Atom Count: 18
• Complexity: 407

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl 1,6-dihydro-6-oxo-2-phenylpyrimidine-5-carboxylate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN=C(NC1=O)C2=CC=CC=C2

Technology Process of Ethyl 4-hydroxy-2-phenylpyrimidine-5-carboxylate

There total 7 articles about Ethyl 4-hydroxy-2-phenylpyrimidine-5-carboxylate 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%

benzamidine monohydrochloride (1670-14-0) + diethyl 2-ethoxymethylenemalonate (87-13-8) → 4-hydroxy-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester (55613-22-4)

Guidance literature:

With sodium hydroxide; In ethanol; at 100 ℃; for 4h;

DOI:10.1016/j.bmc.2013.09.013

Reference yield: 75.0%

benzamidine monohydrochloride (1670-14-0) + diethyl 2-ethoxymethylenemalonate (87-13-8) → ethyl 4-oxo-2-phenyl-3,4-dihydropyrimidine-5-carboxylic acid (55613-22-4)

Guidance literature:

benzamidine monohydrochloride; With sodium ethanolate; In ethanol; at 20 ℃; for 0.5h;

diethyl 2-ethoxymethylenemalonate; In ethanol; at 20 - 80 ℃;

DOI:10.1002/bkcs.10979

Reference yield: 59.0%

ethyl 4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxilate (38026-46-9) + tributylphenylstannane (960-16-7) → ethyl 4-oxo-2-phenyl-3,4-dihydropyrimidine-5-carboxylic acid (55613-22-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; for 24h; Inert atmosphere; Reflux;

DOI:10.1021/jo1003482

upstream raw materials:

propene-1,1,3,3-tetracarboxylic acid tetraethyl ester

N-hydroxybenzenecarboximidamide

benzamidine monohydrochloride

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

1,6-dihydro-6-oxo-2-phenyl-N-(2-pyridyl)-5-pyrimidinecarboxamide

ethyl 4-chloro-2-phenylpyrimidine-5-carboxylate

FAC

N-benzyl-2-(7-methyl-8-oxo-2-phenyl-7,8-dihydro-9H-purin-9-yl)acetamide

Refernces

• 1、 Goto, Taiji,Shiina, Akiko,Yoshino, Toshiharu,Mizukami, Kiyoshi,Hirahara, Kazuki,Suzuki, Osamu,Sogawa, Yoshitaka,Takahashi, Tomoko,Mikkaichi, Tsuyoshi,Nakao, Naoki,Takahashi, Mizuki,Hasegawa, Masashi,Sasaki, Shigeki. "Synthesis and biological evaluation of 5-carbamoyl-2-phenylpyrimidine derivatives as novel and potent PDE4 inhibitors". . p. 7025 - 7037. Retrieved 2013/11/06.
• 2、 -. "AMIDE COMPOUNDS AND USE OF THE SAME". Page/Page column 79. . Retrieved 2012/02/06.