325685-75-4

Basic information

• Product Name: (6-Chloro-2-phenylpyrimidin-4-yl)methanol
• Synonyms: (6-Chloro-2-phenylpyrimidin-4-yl)methanol;(6-CHLORO-2-PHENYLPYRIMIDIN-4-YL)METHANOL(WXG03496)
• CAS NO: 325685-75-4
• Molecular Formula: C₁₁H₉ClN₂O
• Molecular Weight: 221
• Mol File: 325685-75-4.mol

Chemical Properties

• Boiling Point: 290.0±22.0 °C(Predicted)
• Appearance: /
• Density: 1.321±0.06 g/cm3(Predicted)
• PKA: 12.32±0.10(Predicted)
• CAS DataBase Reference: (6-Chloro-2-phenylpyrimidin-4-yl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (6-Chloro-2-phenylpyrimidin-4-yl)methanol(325685-75-4)
• EPA Substance Registry System: (6-Chloro-2-phenylpyrimidin-4-yl)methanol(325685-75-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 325685-75-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(6-Chloro-2-phenylpyrimidin-4-yl)methanol is utilized as a building block in organic synthesis for the creation of a variety of biologically active compounds. Its unique structure allows it to be a versatile component in the synthesis of new molecules with potential applications in various industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (6-Chloro-2-phenylpyrimidin-4-yl)methanol is employed as a key intermediate in the development of new drugs. Its potential pharmacological activities, such as anti-inflammatory and anti-tumor properties, make it a promising candidate for drug development. Researchers are exploring its use in the synthesis of compounds that could treat a range of diseases, particularly those with inflammatory or neoplastic origins.
Used in Drug Development:
(6-Chloro-2-phenylpyrimidin-4-yl)methanol is also used in drug development as a precursor for the synthesis of pharmaceuticals with therapeutic potential. Its chemical properties and reactivity make it suitable for the creation of new drug candidates that could be effective in treating specific medical conditions, pending further research and clinical trials.

Upstream product

• 339278-89-6 6-methoxymethyl-2-phenylpyrimidin-4-ol 
• 618-39-3 benzamidin 
• 1670-14-0 benzamidine monohydrochloride 
• 127958-19-4 4-(methoxymethyl)-2-phenylpyrimidine 
• 325685-59-4 4-chloro-6-methoxymethyl-2-phenylpyrimidine 

Downstream Products

• 913951-70-9 4-{(S)-4-tert-butoxycarbonyl-2-[(2-phenyl-6-pyridin-4-yl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester 
• 913951-69-6 4-{(S)-4-tert-butoxycarbonyl-2-[(2-phenyl-6-pyridin-3-yl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester 
• 913948-93-3 4-{(S)-4-tert-butoxycarbonyl-2-[(2,6-diphenyl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester 
• 913952-11-1 C₂₆H₃₂N₆O₈ 
• 913950-00-2 4-((S)-4-tert-butoxycarbonyl-2-{[6-(3-hydroxy-prop-1-ynyl)-2-phenyl-pyrimidine-4-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester 
• 913947-39-4 C₂₇H₃₇N₇O₆ 
• 913947-43-0 C₂₉H₃₉N₇O₇ 
• 913947-73-6 4-{(S)-4-carboxy-2-[(2-phenyl-6-piperidin-1-yl-pyrimidine-4-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester 
• 913949-21-0 C₂₇H₃₄N₆O₇ 
• 913950-04-6 4-((S)-4-tert-butoxycarbonyl-2-{[6-(3-hydroxy-propyl)-2-phenyl-pyrimidine-4-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester 
• 913950-35-3 4-((S)-4-carboxy-2-{[6-(4-methyl-pyrazol-1-yl)-2-phenyl-pyrimidine-4-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester 
• 913950-12-6 4-((S)-4-tert-butoxycarbonyl-2-{[6-(4-oxo-cyclohexyl)-2-phenyl-pyrimidine-4-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester 
• 913950-09-1 4-((S)-4-carboxy-2-{[6-(4-oxo-cyclohexyl)-2-phenyl-pyrimidine-4-carbonyl]-amino}-butyryl)-piperazine-1-carboxylic acid ethyl ester 

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.

Optimization of 2-phenyl-pyrimidine-4-carboxamides towards potent, orally bioavailable and selective P2Y12 antagonists for inhibition of platelet aggregation

2-Phenyl-pyrimidine-4-carboxamide analogs were identified as P2Y 12 antagonists. Optimization of the carbon-linked or nitrogen-linked substituent at the 6-position of the pyrimidine ring provided compounds with excellent ex vivo potency in the

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).

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

The invention relates to 2-phenyl-6-aminbcarbonyl-pyrimidinc 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 (1).

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