27420-41-3

Basic information

• Product Name: 4-hydroxy-2H-pyrido[1,2-a]pyrimidin-2-one
• Synonyms: 2H-pyrido[1,2-a]pyrimidin-2-one, 4-hydroxy-
• CAS NO: 27420-41-3
• Molecular Formula: C₈H₆N₂O₂
• Molecular Weight: 162.1454
• Mol File: 27420-41-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 320.6°C at 760 mmHg
• Flash Point: 147.7°C
• Density: 1.41g/cm³
• Vapor Pressure: 2.54E-05mmHg at 25°C
• Refractive Index: 1.676
• CAS DataBase Reference: 4-hydroxy-2H-pyrido[1,2-a]pyrimidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-2H-pyrido[1,2-a]pyrimidin-2-one(27420-41-3)
• EPA Substance Registry System: 4-hydroxy-2H-pyrido[1,2-a]pyrimidin-2-one(27420-41-3)

Safety Data

• Hazardous Substances Data: 27420-41-3(Hazardous Substances Data)

Usage

General Description

4-hydroxy-2H-pyrido[1,2-a]pyrimidin-2-one is a chemical compound with the molecular formula C6H5N3O2. It is a derivative of pyrido[1,2-a]pyrimidin-2-one and is an intermediate in the synthesis of various pharmaceutical drugs. 4-hydroxy-2H-pyrido[1,2-a]pyrimidin-2-one is used in the development of antiviral medications and has potential applications in the treatment of infections caused by RNA viruses. It acts by inhibiting viral RNA polymerase, making it a promising target for the development of new antiviral drugs. Additionally, 4-hydroxy-2H-pyrido[1,2-a]pyrimidin-2-one has been studied for its potential neuroprotective and anti-inflammatory properties, showing promise for the treatment of neurodegenerative diseases and inflammatory conditions.

Upstream product

• 886-60-2 1-(2'-pyridyl)-3-phenylthiourea 
• 1663-67-8 malonoyl dichloride 
• 504-29-0 2-aminopyridine 
• 105-53-3 diethyl malonate 
• 138305-21-2 ethyl 3-oxo-3-(pyridin-2-ylamino)propianoate 
• 15781-70-1 malonic acid bis-(2,4,6-trichloro-phenyl) ester 

Downstream Products

• 181938-91-0 2,4-Dichloro-benzoic acid 4-oxo-4H-pyrido[1,2-a]pyrimidin-2-yl ester 
• 247237-88-3 3-dimethylaminothiocarbonylthio-2-hydroxy-pyrido[1,2-a]pyrimidin-4-one 
• 5418-94-0 2-chloro-4H-pyrido[1,2-a]pyrimidin-4-one 
• 5654-95-5 1H-pyrrolo[2,3-b]pyridine-2,3-dione 
• 17481-62-8 2-chloro-4-oxo-4H-pyrido<1,2-a>pyrimidine 3-carboxaldehyde 

Relevant articles and documents

Substituted pyridopyrimidinones, 1: Convenient PTC alkylation and halogenation of 2-hydroxy-4H-pyrido[1,2-a]pyrimidin-4-one

Alkylation of 2-hydroxy-4H-pyrido[1,2-a]-pyrimidin-4-one (1) was investigated under solid-liquid phase transfer catalysis conditions (PTC), using tetrabutylammonium bromide and potassium carbonate. The reaction with alkyl halides led to the formation of various 2-alkoxy products, in fair yields. Reaction of compound 1 with epichlorohydrin and chloroacetonitrile, under the same PTC conditions, afforded novel O1,O3-disubstituted glycerol and oxazolopyridopyrimidone betaine derivatives, respectively. Some 3-halo-, 3,3-dihalo, and/or 2,3-dihalopyrido[1,2-a]pyrimidines were also prepared using different halogenating agents at different reaction conditions.

Discovery and Characterization of (R)-6-Neopentyl-2-(pyridin-2-ylmethoxy)-6,7-dihydropyrimido[2,1-c][1,4]oxazin-4(9H)-one (PF-06462894), an Alkyne-Lacking Metabotropic Glutamate Receptor 5 Negative Allosteric Modulator Profiled in both Rat and Nonhuman Primates

We previously observed a cutaneous type IV immune response in nonhuman primates (NHP) with the mGlu5 negative allosteric modulator (NAM) 7. To determine if this adverse event was chemotype- or mechanism-based, we evaluated a distinct series of mGlu5 NAMs. Increasing the sp3 character of high-throughput screening hit 40 afforded a novel morpholinopyrimidone mGlu5 NAM series. Its prototype, (R)-6-neopentyl-2-(pyridin-2-ylmethoxy)-6,7-dihydropyrimido[2,1-c][1,4]oxazin-4(9H)-one (PF-06462894, 8), possessed favorable properties and a predicted low clinical dose (2 mg twice daily). Compound 8 did not show any evidence of immune activation in a mouse drug allergy model. Additionally, plasma samples from toxicology studies confirmed that 8 did not form any reactive metabolites. However, 8 caused the identical microscopic skin lesions in NHPs found with 7, albeit with lower severity. Holistically, this work supports the hypothesis that this unique toxicity may be mechanism-based although additional work is required to confirm this and determine clinical relevance.

QUINAZOLINONE COMPOUNDS AND DERIVATIVES THEREOF

Compounds of Formula I are useful inhibitors of tankyrase. Compounds of Formula I have the following structure: where the definitions of the variables are provided herein.