118996-61-5

Basic information

• Product Name: 4-CHLORO-6-(METHYLSULFANYL)-2-PHENYL-5-PYRIMIDINECARBONITRILE
• Synonyms: 4-CHLORO-6-(METHYLTHIO)-2-PHENYLPYRIMIDINE-5-CARBONITRILE;4-CHLORO-6-(METHYLSULFANYL)-2-PHENYL-5-PYRIMIDINECARBONITRILE;4-CHLORO-5-CYANO-6-(METHYLTHIO)-2-PHENYLPYRIMIDINE
• CAS NO: 118996-61-5
• Molecular Formula: C₁₂H₈ClN₃S
• Molecular Weight: 261.73
• Mol File: 118996-61-5.mol

Chemical Properties

• Boiling Point: 327.5°Cat760mmHg
• Flash Point: 151.9°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 0.000201mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: 4-CHLORO-6-(METHYLSULFANYL)-2-PHENYL-5-PYRIMIDINECARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-6-(METHYLSULFANYL)-2-PHENYL-5-PYRIMIDINECARBONITRILE(118996-61-5)
• EPA Substance Registry System: 4-CHLORO-6-(METHYLSULFANYL)-2-PHENYL-5-PYRIMIDINECARBONITRILE(118996-61-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 118996-61-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H8ClN3S/c1-17-12-9(7-14)10(13)15-11(16-12)8-5-3-2-4-6-8/h2-6H,1H3

Upstream product

• 15908-64-2 3,4-dihydro-6-methymercapto-4-oxo-2-phenylpyrimidine-5-carbonitrile 
• 17823-58-4 ethyl 2-cyano-3,3-di(methylsulfanyl)acrylate 
• 618-39-3 benzamidin 
• 1670-14-0 benzamidine monohydrochloride 
• 5147-80-8 [Bis(methylthio)methylene]malononitrile 
• 3490-92-4 methyl 2-cyano-3,3-bis(methylsulfanyl)acrylate 
• 55-21-0 benzamide 

Downstream Products

• 118996-64-8 6-methylthio-4-morpholino-2-phenylpyrimidine-5-carbonitrile 
• 1055922-67-2 4-(3-Methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-ylamino)-6-(methylthio)-2-phenylpyrimidine-5-carbonitrile 
• 1055923-50-6 4-(4-methyl-3,6-dioxo-3,6-dihydropyridazin-1(2H)-yl)-6-(methylthio)-2-phenylpyrimidine-5-carbonitrile 
• 1632027-90-7 ethyl 4-((ethoxycarbonyl)(mercapto)methylene)-7-amino-3,4-dihydro-2-phenylthieno[3,2-d]pyrimidine-6-carboxylate 
• 1632027-88-3 ethyl 2-(5-cyano-6-(methylthio)-2-phenylpyrimidin-4-ylthio)acetate 
• 1055923-47-1 C₁₂H₁₁N₅S 
• 118996-77-3 5-cyano-4-hydrazino-6-morpholino-2-phenylpyrimidine 
• 118996-71-7 6-anilino-4-methylthio-2-phenylpyrimidine-5-carboxaldehyde 
• 118996-78-4 5-amino-4-hydrazino-2-phenyl-7H-pyrazolo<3,4-d>pyrimidine 
• 118996-72-8 4-hydroxy-2-phenylpyrimido<4,5-b>quinoline 
• 118996-67-1 methyl 1-cyano-1-(5-cyano-4-methylthio-2-phenylpyrimidin-6-yl)acetate 
• 118996-69-3 1-cyano-1-(5-cyano-4-methylthio-2-phenylpyrimidin-6-yl)acetonitrile 
• 118996-76-2 3-amino-4-methylthio-2,6-diphenylpyrazolo<3,4-d>pyrimidine 
• 118996-68-2 ethyl 1-cyano-1-(5-cyano-4-methylthio-2-phenylpyrimidin-6-yl)acetate 

Relevant articles and documents

A convenient synthesis of pyrimidinone and pyrimidine containing bisheteroarenes and analogs

The synthesis of pyrimidinone containing bisheteroarenes (3) and related analogs (9 and 10) by the reaction of active methylenes or substituted methyl acrylate with nitrogen containing precursors viz. amidines, or thiourea in water as well as other organic solvents was studied. Synthesized compounds have further been explored for the synthesis of diversified pyrimidines 4, 6-8, 11, 12 and 14 through a sequential approach. This journal is the Partner Organisations 2014.

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.).

New heterocyclic compounds

Provided herein are heterocyclic compounds of the general formula (I), their derivatives, analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, pharmaceutically acceptable salts and compositions, metabolites and prodrugs thereof, wherein R1, R2, R3, R4 and R5 are as described herein. Further described herein in particular are heterocyclic compounds of the formula (I) for treating various diseases. and disorders by administering in a patient one or more TNF-α, Thromboxane synthase, 5-LOX, and PDE4 inhibitors. In particular described herein are methods for treating immunological diseases, inflammation, pain disorder, rheumatoid arthritis; osteoporosis; multiple myeloma; uveititis; acute and chronic myelogenous leukemia; ischemic heart disease; atherosclerosis; cancer; ischemic-induced cell damage; pancreatic beta cell destruction; osteoarthritis; rheumatoid spondylitis; gouty arthritis; inflammatory bowel disease; adult respiratory distress syndrome (ARDS); psoriasis; Crohn's disease; allergic rhinitis; ulcerative colitis; anaphylaxis; contact dermatitis; muscle degeneration; cachexia; asthma; bone resorption diseases; ischemia reperfusion injury; brain trauma; multiple sclerosis; sepsis; septic shock; toxic shock syndrome; fever, and myalgias due to infection and diseases mediated by HIV-1; HIV-2; HIV-3; cytomegalovirus (CMV); influenza; adenovirus; the herpes viruses (including HSV-1, HSV-2) and herpes zoster viruses in a mammal comprising administering an effective amount of a compound of formula (I).

Suitably functionalised pyrimidines as potential antimycotic agents

Various suitably functionalised pyrimidine derivatives have been synthesized to explore their potential as antimycotic agents. Some of the synthesized compounds 4c, 4d, 8a-e have shown highly significant in vitro antifungal activity against five human pathogenic fungi. (C) 2000 Elsevier Science Ltd. All rights reserved.

Chemotherapeutic agents: Part XXIII - Synthesis of π-deficient pyrimidines and fused pyrimidines as leishmanicides

Various ?-deficient pyrimidines and fused purimidines have been synthesized and evaluated for their leishmanicidal activity against L. donovani.

Synthesis of Pyrimidine Derivatives by the Reaction of Ketene Dithioacetals with Amides

Reactions of methyl 2-cyano-3,3-bis(methylthio)acrylate (1a) with carboxamides 2a-g in the presence of sodium hydride in a mixture of benzene and N,N-dimethylacetamide took place displacement with the methylthio group to give the corresponding methyl 3-N-acylamino-2-cyano-3-(methylthio)acrylates 3a-g which were readily converted to the corresponding pyrimidine derivatives at reflux in methanol in good yields.Reactions of 2-cyano-3,3-bis(methylthio)acrylonitrile (1b) with the carboxamides 2a-f gave directly pyrimidine-5-carbonitrile derivatives 7a-f.Ketene dithioacetals 1a,b smoothly reacted with thioamide 2g or urea 2h,i to give the expected pyrimidine derivatives 9,10a,b.Polyfunctionalized pyrimidines, thus obtained, were also used for the synthesis of fused pyrimidine derivatives.