325685-59-4

Basic information

• Product Name: 4-CHLORO-6-(METHOXYMETHYL)-2-PHENYLPYRIMIDINE
• Synonyms: 4-Chloro-6-(methoxymethyl)
• CAS NO: 325685-59-4
• Molecular Formula: C₁₂H₁₁ClN₂O
• Molecular Weight: 234.69
• Mol File: 325685-59-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 54-56°
• Boiling Point: 258.5°Cat760mmHg
• Flash Point: 110.1°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 0.0221mmHg at 25°C
• Refractive Index: 1.571
• PKA: -1.37±0.32(Predicted)
• CAS DataBase Reference: 4-CHLORO-6-(METHOXYMETHYL)-2-PHENYLPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-6-(METHOXYMETHYL)-2-PHENYLPYRIMIDINE(325685-59-4)
• EPA Substance Registry System: 4-CHLORO-6-(METHOXYMETHYL)-2-PHENYLPYRIMIDINE(325685-59-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 325685-59-4(Hazardous Substances Data)

Usage

General Description

4-CHLORO-6-(METHOXYMETHYL)-2-PHENYLPYRIMIDINE is a chemical compound with the molecular formula C12H11ClN2O. It consists of a pyrimidine ring with a chloro group at the 4th position, a methoxymethyl group at the 6th position, and a phenyl group at the 2nd position. 4-CHLORO-6-(METHOXYMETHYL)-2-PHENYLPYRIMIDINE is often used in the pharmaceutical industry as a building block for the synthesis of various drugs, especially those with antiviral and anticancer properties. It is also used as an intermediate in the production of agrochemicals and other fine chemicals. Due to its versatile applications, 4-CHLORO-6-(METHOXYMETHYL)-2-PHENYLPYRIMIDINE is considered an important and valuable chemical in the field of organic synthesis.

InChI:InChI=1/C12H11ClN2O/c1-16-8-10-7-11(13)15-12(14-10)9-5-3-2-4-6-9/h2-7H,8H2,1H3

Upstream product

• 339278-89-6 6-methoxymethyl-2-phenylpyrimidin-4-ol 
• 618-39-3 benzamidin 
• 66762-68-3 ethyl 4-methoxy-3-oxobutanoate 
• 1670-14-0 benzamidine monohydrochloride 
• 41051-15-4 4-methoxyacetoacetic acid methylester 
• 127958-19-4 4-(methoxymethyl)-2-phenylpyrimidine 

Downstream Products

• 325685-75-4 4-Chloro-6-hydroxymethyl-2-phenylpyrimidine 
• 922726-27-0 4-methoxymethyl-2-phenyl-6-(pyridin-2-yl)pyrimidine 
• 922726-19-0 1-(6-(methoxymethyl)-2-phenylpyrimidin-4-yl)-1-methylhydrazine 
• 922726-28-1 6-(6-methoxymethyl-2-phenylpyrimidin-4-yl)-2,2'-bipyridine 
• 922726-32-7 2-phenyl-6-(pyridin-2-yl)pyrimidine-4-carbaldehyde 
• 922726-29-2 (2-phenyl-6-(pyridin-2-yl)pyrimidin-4-yl)methanol 
• 922726-31-6 6-(2,2'-bipyridin-6-yl)-2-phenylpyrimidine-4-carbaldehyde 
• 922726-30-5 (6-(2,2'-bipyridin-6-yl)-2-phenylpyrimidin-4-yl)methanol 
• 325685-60-7 1-(6-Methoxymethyl-2-phenylpyrimidin-4-yl)ethanone 
• 325685-62-9 2-Phenyl-6-(4-propylsulfanyl[2,2']bipyridinyl-6-yl)pyrimidine-4-carbaldehyde 
• 325685-76-5 6-tert-Butyldiphenylsilanoxymethyl-4-chloro-2-phenylpyrimidine 
• 325685-72-1 4-Hydroxymethyl-2-phenyl-6-(4-propylsulfanyl[2,2']bipyridinyl-6-yl)pyrimidine 
• 325685-61-8 6-(6-Methoxymethyl-2-phenylpyrimidin-4-yl)-4-propylsulfanyl[2,2']bipyridinyl 
• 325685-66-3 1-[6-(tert-Butyldiphenylsilanoxymethyl)-2-phenylpyrimidin-4-yl]ethanone 

Relevant articles and documents

4-((R)-2-{[6-((S)-3-Methoxypyrrolidin-1-yl)-2-phenylpyrimidine-4-carbonyl]amino}-3-phosphonopropionyl)piperazine-1-carboxylic Acid Butyl Ester (ACT-246475) and Its Prodrug (ACT-281959), a Novel P2Y12 Receptor Antagonist with a Wider Therapeutic Window in the Rat Than Clopidogrel

Recent post hoc analyses of several clinical trials with P2Y12 antagonists showed the need for new molecules being fully efficacious as antiplatelet agents and having a reduced propensity to cause major bleeding. We have previously reported the discovery of the 2-phenylpyrimidine-4-carboxamide analogs as P2Y12 antagonists with nanomolar potency in the disease-relevant platelet aggregation assay in human plasma. Herein we present the optimization steps that led to the discovery of clinical candidate ACT-246475 (30d). The key step was the replacement of the carboxylic acid functionality by a phosphonic acid group which delivered the most potent molecules of the program. In addition, low in vivo clearance in rat and dog was achieved for the first time. Since the bioavailability of 30d was low in rat and dog, we developed the bis((isopropoxycarbonyl)oxy)methyl ester prodrug (ACT-281959, 45). Compound 30d showed efficacy in the rat ferric chloride thrombosis model when administered intravenously as parent or orally as its prodrug 45. Moreover, 30d displays a wider therapeutic window as compared to clopidogrel in the rat surgical blood loss model.

2-PHENYL-6-AMINOCARBONYL-PYRIMIDINE DERIVATIVES AND THEIR USE AS P2Y12 RECEPTOR ANTAGONISTS

The invention relates to 2-phenyl-6-aminocarbonyl-pyrimidine derivatives and their use as P2Y12 receptor antagonists in the treatment and/or prevention and/or treatment of peripheral vascular, of visceral-, hepatic- and renal-vascular, of cardiovascular and of cerebrovascular diseases or conditions associated with platelet aggregation, including thrombosis in humans and other mammals. Formula (I).

Enforced helicity: Efficient access to self-organized helical molecular strands by the imine route

The condensation of the two oligoheterocyclic aldehydes 8 and 16 with the bis-hydrazine 17 gives the bis-hydrazones 1 and 2. These molecular strands are shown to adopt helical conformations of 1.5 and 2.5 turns, respectively. The helical shape of 1 has be