4840-69-1

Basic information

• Product Name: 5-fluoro-3-methyl-1H-pyrimidine-2,4-dione
• Synonyms: 5-fluoro-3-methyl-1H-pyrimidine-2,4-dione
• CAS NO: 4840-69-1
• Molecular Formula: C5H5FN2O2
• Molecular Weight: 144.1
• Mol File: 4840-69-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.44g/cm³
• Refractive Index: 1.526
• PKA: 9.32±0.10(Predicted)
• CAS DataBase Reference: 5-fluoro-3-methyl-1H-pyrimidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-fluoro-3-methyl-1H-pyrimidine-2,4-dione(4840-69-1)
• EPA Substance Registry System: 5-fluoro-3-methyl-1H-pyrimidine-2,4-dione(4840-69-1)

Safety Data

• Hazardous Substances Data: 4840-69-1(Hazardous Substances Data)

Usage

General Description

5-fluoro-3-methyl-1H-pyrimidine-2,4-dione is a chemical compound with the molecular formula C5H5FN2O2. It is a pyrimidine derivative with the fluorine and methyl substituents at the 5 and 3 positions, respectively. 5-fluoro-3-methyl-1H-pyrimidine-2,4-dione is used as a precursor in the synthesis of various pharmaceuticals and agrochemicals. It has also been studied for its potential therapeutic applications, including as an anti-cancer agent and for the treatment of neurodegenerative diseases. Additionally, it has been investigated for its antimicrobial and antifungal properties. Due to its versatile nature and potential pharmaceutical applications, 5-fluoro-3-methyl-1H-pyrimidine-2,4-dione is a compound of interest in the field of medicinal chemistry and drug development.

InChI:InChI=1/C5H5FN2O2/c1-8-4(9)3(6)2-7-5(8)10/h2H,1H3,(H,7,10)

Upstream product

• 1431628-10-2 tert-butyl 5-fluoro-3-methyl-2,4-dioxo-pyrimidine-1-carboxylate 
• 93075-27-5 5-Fluoro-1-methyl-pyrimidine-2,4,6-trione 
• 13593-37-8 6-chloro-5-fluoro-3-methyl-1H-pyrimidine-2,4-dione 
• 118004-25-4 Carbonic acid benzyl ester 5-fluoro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl ester 
• 115923-75-6 Acetic acid 5-fluoro-1-methyl-2,6-dioxo-hexahydro-pyrimidin-4-yl ester 
• 51-21-8 5-fluorouracil 
• 74-88-4 methyl iodide 
• 608-34-4 3-methyluracil 
• 78948-09-1 acetyl hypofluorite 

Relevant articles and documents

Discovery of a new class of highly potent inhibitors of acid ceramidase: Synthesis and structure-activity relationship (SAR)

Acid ceramidase (AC) is an intracellular cysteine amidase that catalyzes the hydrolysis of the lipid messenger ceramide. By regulating ceramide levels in cells, AC may contribute to the regulation of cancer cell proliferation and senescence and to the response to cancer therapy. We recently identified the antitumoral agent carmofur (4a) as the first nanomolar inhibitor of intracellular AC activity (rat AC, IC50 = 0.029 μM). In the present work, we expanded our initial structure-activity relationship (SAR) studies around 4a by synthesizing and testing a series of 2,4-dioxopyrimidine-1- carboxamides. Our investigations provided a first elucidation of the structural features of uracil derivatives that are critical for AC inhibition and led us to identify the first single-digit nanomolar inhibitors of this enzyme. The present results confirm that substituted 2,4-dioxopyrimidine-1-carboxamides are a novel class of potent inhibitors of AC. Selected compounds of this class may represent useful probes to further characterize the functional roles of AC.

New tetramethyl-cis-diaza-bicyclo{4.2.0}octane-3,5-dione derivatives having differentiation-inducing activity and antiviral activity

As new compounds are now provided 7,7,8,8,-tetramethyl-cis-diaza-bicyclo{4.2.0}octane-3,5,-dione derivatives which have an activity to induce the differentiation of tumor cells and are useful as antitumor agent, and which also have an antiviral activity against various viruses and are useful as antiviral agent. These new derivatives may be produced by a photo-addition reaction of a uracil compound with 2,3-dimethyl-2-butene.

Glorination of Pyrimidines. Part 2. Mechanistic Aspects of the Reaction of Acetyl Hypofluorite with Uracil and Cytosine Derivatives

The reaction of acetyl hypofluorite (AcOF) with uracil, cytosine, and some N-1-substituted derivatives dissolved in either acetic acid or water has been investigated.Analysis by radio-h.p.l.c., using (18)f as a tracer, and by (1)H n.m.r. revealed that a substituent at N-1 of uracil has a remarkable effect on the stability of the intermediate 6-acetoxy-5-fluoro-5,6-dihydrouracils.In addition, it was found that these cytosine adducts rapidly deaminate in water yielding their corresponding uracil analogues.