36746-06-2

Basic information

• Product Name: ethyl 4-chloro-6-methyl-2-phenyl-pyrimidine-5-carboxylate
• Synonyms: ethyl 4-chloro-6-methyl-2-phenyl-pyrimidine-5-carboxylate
• CAS NO: 36746-06-2
• Molecular Weight: 276.722
• Mol File: 36746-06-2.mol

Chemical Properties

• CAS DataBase Reference: ethyl 4-chloro-6-methyl-2-phenyl-pyrimidine-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-chloro-6-methyl-2-phenyl-pyrimidine-5-carboxylate(36746-06-2)
• EPA Substance Registry System: ethyl 4-chloro-6-methyl-2-phenyl-pyrimidine-5-carboxylate(36746-06-2)

Safety Data

• Hazardous Substances Data: 36746-06-2(Hazardous Substances Data)

Upstream product

• 23155-55-7 ethyl 4-mercapto-6-methyl-2-phenyl-5-pyrimidinecarboxylate 
• 1462-12-0 diethyl ethylidenemalonate 
• 1670-14-0 benzamidine monohydrochloride 

Downstream Products

• 178380-71-7 ethyl 6-[(4-methoxyphenyl)amino]-4-methyl-2-phenylpyrimidine-5-carboxylate 
• 94037-15-7 ethyl 6-methyl-2-phenyl-4-phenylamino-5-pyrimidine carboxylate 
• 128072-68-4 ethyl 4-amino-6-methyl-2-phenylpyrimidine-5-carboxylate 

Relevant articles and documents

Synthesis and biological evaluation of 5-carbamoyl-2-phenylpyrimidine derivatives as novel and potent PDE4 inhibitors

5-Carbamoyl-2-phenylpyrimidine derivative 2 has been identified as a phosphodiesterase 4 (PDE4) inhibitor with moderate PDE4B inhibitory activity (IC50 = 200 nM). Modification of the carboxylic acid moiety of 2 gave N-neopentylacetamide derivative 10f, which had high in vitro PDE4B inhibitory activity (IC50 = 8.3 nM) and in vivo efficacy against lipopolysaccharide (LPS)-induced pulmonary neutrophilia in mice (ID50 = 16 mg/kg, ip). Furthermore, based on the X-ray crystallography of 10f bound to the human PDE4B catalytic domain, we designed 7,8-dihydro-6H-pyrido[4,3-d] pyrimidin-5-one derivative 39 which has a fused bicyclic lactam scaffold. Compound 39 exhibited excellent inhibitory activity against LPS-induced tumor necrosis factor alpha (TNF-α) production in mouse splenocytes (IC 50 = 0.21 nM) and in vivo anti-inflammatory activity against LPS-induced pulmonary neutrophilia in mice (41% inhibition at a dose of 1.0 mg/kg, i.t.).

Some reactions with ethyl 4-(mercapto/ chloro)-6-methyl-2-phenylpyrimidine-5-carboxylate

Michael adducts (2a,b), transesters, 4a,b and/or chloropyrimidine (5) have been synthesized from 4-mercaptopyrimidine (1). Compound 5 on reaction with ethyl glycinate, arylamines, 2-aminopyridine, ammonium acetate, acid hydrazide, hydrazine, and/or benzilmonohydrazone gives pyrrolopyrimidine (8), 4-arylaminopyrimidines (9a,b), pyridylaminopyrimidine (11), 4-aminopyrimidine (13), 4-aroylhydrazinopyrimidine (15a,b), 1,2-bis(substituted phenylpyrimidine-4-yl)hydrazine (19) and/or pyrimidopyridazine (20), respectively. ? Present address: Chemistry Department, Faculty of Science, Cairo University, AR Egypt.