79387-69-2

Basic information

• Product Name: 5-Iodo-2-pyrimidone
• Synonyms: 2-Hydroxy-5-Iodopyrimidine;2(1H)-Pyrimidinone, 5-iodo-;5-IodopyriMidin-2(1H)-one;5-iodo-1H-pyrimidin-2-one;5-Iodopyrimidin-2(1H);5-Iodo-2-pyrimidone
• CAS NO: 79387-69-2
• Molecular Formula: C₄H₃IN₂O
• Molecular Weight: 221.98
• Mol File: 79387-69-2.mol

Chemical Properties

• Boiling Point: 393.6ºC at 760 mmHg
• Flash Point: 191.8ºC
• Appearance: /
• Density: 2.403g/cm3
• Vapor Pressure: 9.28E-07mmHg at 25°C
• Refractive Index: 1.761
• Storage Temp.: 2-8°C(protect from light)
• PKA: 7.86±0.10(Predicted)
• CAS DataBase Reference: 5-Iodo-2-pyrimidone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Iodo-2-pyrimidone(79387-69-2)
• EPA Substance Registry System: 5-Iodo-2-pyrimidone(79387-69-2)

Safety Data

• Hazardous Substances Data: 79387-69-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
5-Iodo-2-pyrimidone is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique chemical structure allows it to be a building block for the development of new drugs and pesticides, contributing to advancements in healthcare and agriculture.
Used in Dye and Pigment Production:
In the dye and pigment industry, 5-Iodo-2-pyrimidone is utilized for the production of dyes and pigments. Its chemical properties make it suitable for creating a range of colors and hues, enhancing the color palette available for various applications.
Used in Drug Development:
5-Iodo-2-pyrimidone exhibits potential anti-bacterial properties and is under research for its potential use in drug development. Its ability to combat bacterial infections could lead to the creation of new antibiotics, addressing the growing need for effective treatments against resistant bacteria.
Overall, 5-Iodo-2-pyrimidone is a multifaceted chemical compound with applications spanning across pharmaceuticals, agrochemicals, dyes and pigments, and drug development, showcasing its importance in various industries.

InChI:InChI=1/C4H3IN2O/c5-3-1-6-4(8)7-2-3/h1-2H,(H,6,7,8)

Synthetic route

2-hydroxypyrimidine hydrochloride (38353-09-2) → 5-iodo-2(1H)-pyrimidinone (79387-69-2)

Conditions	Yield
With methanol; iodine; silver sulfate at 20℃; for 16h; Darkness;	94%

Pyrimidin-2(1H)-one (557-01-7) → 5-iodo-2(1H)-pyrimidinone (79387-69-2)

Conditions	Yield
With N-iodo-succinimide In N,N-dimethyl-formamide for 48h; Ambient temperature;	77.5%
With N-iodo-succinimide In N,N-dimethyl-formamide	11.35 g (77.5%)
With N-iodo-succinimide In N,N-dimethyl-formamide	11.35 g (77.5%)

2-pyrimidinone hydrochloride (38353-09-2) → 5-iodo-2(1H)-pyrimidinone (79387-69-2)

Conditions	Yield
With sodium dihydrogen phosphate; sodium iodine dichloride In water at 65℃; for 1.66667h;	75%
With Iodine monochloride; sodium chloride In water at 60℃; for 1h;
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 48h;
With Iodine monochloride; acetic acid In water at 45 - 48℃; for 6h; Temperature;

Upstream product

• 557-01-7 Pyrimidin-2(1H)-one 
• 38353-09-2 2-pyrimidinone hydrochloride 
• 38353-09-2 2-hydroxypyrimidine hydrochloride 

Downstream Products

• 116519-90-5 1-benzyloxymethyl-5-iodo-2(1H)-pyrimidinone 
• 116392-90-6 5-iodo-1-phenoxymethyl-2(1H)-pyrimidinone 
• 83768-02-9 2-(4-chlorophenoxy)methoxy-5-iodopyrimidine 
• 83768-03-0 1-(4-chlorophenoxy)methyl-5-iodopyrimidin-2-one 
• 116392-93-9 5-iodo-12-phenylsulfenylmethyl-2(1H)-pyrimidinone 
• 32779-38-7 2-chloro-5-iodopyrimidine 
• 38953-72-9 5-iodo-2,4-bis-O-trimethylsilyluracil 
• 1198745-16-2 5-iodo-2-[((1R)-1-methyl-2-{3-[(1-methylethyl)oxy]phenyl}ethyl)oxy]pyrimidine 
• 96245-84-0 1-<3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl>-5-iodo-2-pyrimidinone 
• 103594-69-0 1-benzyl-5-iodopyrimidin-2-(1H)-one 

Relevant articles and documents

Preparation method of 1-(2-deoxy-beta-D-ribofuranose)-5-iodo-2-pyrimidone

The invention relates to 1-(2-deoxidized-beta-D-ribofuranose)-5-iodo-2-pyrimidone, and particularly relates to a preparation method of 1-(2-deoxidized-beta-D-ribofuranose)-5-iodo-2-pyrimidone. The preparation method comprises the following steps of performing a reaction on 2-hydroxypyrimidine hydrochloride and a glacial acetic acid/iodine monochloride solution so as to generate 5-iodo-2-pyrimidone; performing a reaction on the 5-iodo-2-pyrimidone and 1-chloro-3,5-di(4-chlorbenzoyl)-2-deoxy-D-ribose so as to generate 1-[(3,5-di(4-chlorbenzoyl)-2-deoxy-beta-D-erythro-pentofuranose]-5-iodo-2-pyrimidone; and finally generating a target product by using the 1-[(3,5-di(4-chlorbenzoyl)-2-deoxy-beta-D-erythro-pentofuranose]-5-iodo-2-pyrimidone. All intermediates are stable, the yield is high, andthe method is suitable for industrial production.

IDOXURIDINE AND ITS ANALOGS AS NEUROPROTECTANS FOR THE TREATMENT OF PARKINSONISM

The invention relates to compounds that are useful in the treatment of parkinsonism, such as parkinsonism in connection with Parkinson's disease (PD); dementia with Lewy bodies (DLB); multiple system atrophy (MSA); corticobasal degeneration (CBD); or progressive supranuclear palsy (PSP). The said compounds include in particular idoxuridineand analogs thereofas well as their metabolic precursors, such as ropidoxuridine.The invention further relates to method for identifying compounds useful for the treatment of parkinsonism, said methods comprising detecting the capability of compound to increase the amount of GPR37 in cell membranes.The invention further relates to methods for the chemical synthesis of ropidoxuridine.

Evaluation of α-pyrones and pyrimidones as photoaffinity probes for affinity-based protein profiling

α-Pyrones and pyrimidones are common structural motifs in natural products and bioactive compounds. They also display photochemistry that generates high-energy intermediates that may be capable of protein reactivity. A library of pyrones and pyrimidones was synthesized, and their potential to act as photoaffinity probes for nondirected affinity-based protein profiling in several crude cell lysates was evaluated. Further "proof-of-principle" experiments demonstrate that a pyrimidone tag on an appropriate scaffold is equally capable of proteome labeling as a benzophenone.

Development of a concise scaleable synthesis of 2-chloro-5-(pyridin-2-yl) pyrimidine via a Negishi cross-coupling

A practical and scaleable synthesis of 2-chloro-5-(pyridin-2-yl) pyrimidine, an intermediate in the synthesis of a selective PDE-V inhibitor, was developed. A Negishi cross-coupling between the in situ prepared 2-pyridylzinc chloride and 5-iodo-2-chloropyrimidine catalyzed by Pd(PPh3)4 afforded the product in one step. Development of a convenient purification did away with the necessity of chromatography, allowing the preparation of the product on kilogram scale.

Chemoselectivity and Regoselectivity in Reactions of Pyrimidines

Selective nucleophilic substitution and hydrogenolysis reactions in pyrimidines are discussed.Stepwise oxidation reactions of pyrimidine sulfides and HPLC studies of these are reported.

Synthesis and Biological Activities of 2-Pyrimidinone Nucleosides. 2. 5-Halo-2-pyrimidinone 2'-Deoxyribonucleosides

1-(2-Deoxy-β-D-ribofuranosyl)-5-bromo-2-pyrimidinone (BrPdR) and 1-(2-deoxy-β-D-ribofuranosyl)-5-iodo-2-pyrimidinone (IPdR) have been synthesized by condensation of the appropriate silylated bases 2a and 2b, respectively, with 3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride (8) in 1,2-dichloroethane, in the presence of SnCl4, followed by separation of the anomeric blocked nucleosides via column chromatography and subsequent deprotection with methanolic ammonia.Both BrPdR and IPdR exhibited significant antiherpes activities against various strains of HSV-1 and HSV-2, the latter compound (IPdR) showing the higher activity as well as the stronger binding to the virus-specific thimidine kinase.

α-Haloalkyl Ethers in Alkylations of 2-Pyrimidinones

The ambident 5-halopyrimidin-2-one anion with potassium as counterion in DMF is preferentially O-alkylated using the relatively hard α-chloroalkyl ether electrophiles.As ammonium salts in dichloromethane or by the use of KF-alumina in DME the preference is for N-alkylation.TMS ethers of the pyrimidinones are exclusively N-alkylated.