89567-07-7

Basic information

• Product Name: 2-CHLOROMETHYL-5-PHENYL-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE
• Synonyms: 3-(chloroMethyl)-7-phenyl-9-thia-2,4-diazabicyclo[4.3.0]nona-2,7,10-trien-5-one;2-(Chloromethyl)-5-phenylthieno[2,3-d]pyrimidin-4(1H)-one;2-(Chloromethyl)-5-phenylthieno[2,3-d]pyrimidin-4-ol
• CAS NO: 89567-07-7
• Molecular Formula: C₁₃H₉ClN₂OS
• Molecular Weight: 276.741360
• Mol File: 89567-07-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 182 °C
• Appearance: /
• Density: 1.48g/cm³
• Refractive Index: 1.724
• PKA: 10.04±0.20(Predicted)
• CAS DataBase Reference: 2-CHLOROMETHYL-5-PHENYL-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLOROMETHYL-5-PHENYL-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE(89567-07-7)
• EPA Substance Registry System: 2-CHLOROMETHYL-5-PHENYL-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE(89567-07-7)

Safety Data

• Hazardous Substances Data: 89567-07-7(Hazardous Substances Data)

Usage

General Description

2-CHLOROMETHYL-5-PHENYL-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE is a chemical compound with a molecular formula C13H9ClN2OS. It is a heterocyclic organic compound that contains a thiophene ring fused to a pyrimidine ring. 2-CHLOROMETHYL-5-PHENYL-3H-THIENO[2,3-D]PYRIMIDIN-4-ONE is also substituted with a chloromethyl group at the 2-position and a phenyl group at the 5-position of the pyrimidine ring. It is used primarily in the pharmaceutical industry for the synthesis of potential drug candidates and may have various bioactive properties. Its structure makes it a potential candidate for drug development, and it may exhibit a range of pharmacological activities such as antimicrobial, antifungal, and antiviral properties. Additionally, it may also have potential applications in the field of agricultural chemicals.

InChI:InChI=1/C13H9ClN2OS/c14-6-10-15-12(17)11-9(7-18-13(11)16-10)8-4-2-1-3-5-8/h1-5,7H,6H2,(H,15,16,17)

Upstream product

• 4815-36-5 ethyl 2-amino-4-phenyl-thiophene-3-carboxylate 
• 107-14-2 chloroacetonitrile 
• 98-86-2 acetophenone 

Downstream Products

• 1419183-48-4 2-fluoromethyl-5-phenylthieno[2,3-d]pyrimidin-4(3H)-one 
• 1437772-88-7 1-[[4-[4-[[methyl-(1-methylpyrrolidin-3-yl)amino]methyl]-1-piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]methyl]pyrrolidin-2-one 
• 1437774-95-2 1-[[4-[4-(bromomethyl)-1-piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]methyl]pyrrolidin-2-one 
• 1437774-94-1 1-[[4-[4-(hydroxymethyl)-1-piperidyl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]methyl]pyrrolidin-2-one 
• 1437774-93-0 [1-[2-(chloromethyl)-5-phenyl-thieno[2,3-d]pyrimidin-4-yl]-4-piperidyl]methanol 
• 101130-20-5 2-[(E)-2-(4-Nitro-phenyl)-vinyl]-5-phenyl-3H-thieno[2,3-d]pyrimidin-4-one 
• 1182686-05-0 C₂₁H₁₆N₄O₂S₂ 
• 726164-74-5 C₂₀H₁₄N₄OS₂ 
• 1415755-57-5 2-{[(1H-benzimidazol-2-yl)sulfinyl]methyl}-5-phenyl-4-(2,2,2-trifluoroethoxy)thieno[2,3-d]pyrimidine 
• 1415755-54-2 2-{[(1H-benzimidazol-2-yl)sulfinyl]methyl}-4-methoxy-5-phenylthieno[2,3-d]pyrimidine 
• 1415755-73-5 C₂₂H₁₅F₃N₄OS₂ 
• 1415755-72-4 C₂₁H₁₆N₄OS₂ 
• 1415755-85-9 C₂₁H₁₅ClN₄OS₂ 
• 1415755-84-8 C₂₀H₁₃ClN₄S₂ 

Relevant articles and documents

A Thieno[2,3- d]pyrimidine Scaffold Is a Novel Negative Allosteric Modulator of the Dopamine D2 Receptor

Recently, a novel negative allosteric modulator (NAM) of the D2-like dopamine receptors 1 was identified through virtual ligand screening. This ligand comprises a thieno[2,3-d]pyrimidine scaffold that does not feature in known dopaminergic ligands. Herein, we provide pharmacological validation of an allosteric mode of action for 1, revealing that it is a NAM of dopamine efficacy and identify the structural determinants of this allostery. We find that key structural moieties are important for functional affinity and negative cooperativity, while functionalization of the thienopyrimidine at the 5- and 6-positions results in analogues with divergent cooperativity profiles. Successive compound iterations have yielded analogues exhibiting a 10-fold improvement in functional affinity, as well as enhanced negative cooperativity with dopamine affinity and efficacy. Furthermore, our study reveals a fragment-like core that maintains low μM affinity and robust negative cooperativity with markedly improved ligand efficiency.

A novel microwave-assisted green synthesis of condensed 2-substituted-pyrimidin-4(3H)-ones under solvent-free conditions

A rapid microwave-assisted green chemical synthesis of condensed 2-substituted-pyrimidin-4(3H)-ones 3, 4, and 5 involving the condensation of a variety of nitriles with o-aminoesters of thiophene 2a-e, benzene 2f, dimethoxybenzene 2g and quinazolinone 2h in the presence of catalytic amount of HCl alone or with the Lewis acid AlCl3 under solvent-free conditions, is described for the first time. This novel and clean one-pot methodology, which is characterized by very short reaction times and easy workup procedures, can be exploited to generate a diverse library of condensed pyrimidine heterocycles.

THIENOPYRIMIDINE DERIVATIVES AS POTASSIUM CHANNEL INHIBITORS

The present invention provides thienopyrimidine compounds which are potasium channels inhibitors. Pharmaceutical compositions comprising the compounds and their use in the treatment of arrhythmia are also provided.