4160-77-4

Usage

Definition

ChEBI: A pyrimidone that is uracil with methyl group substituents at positions 3 and 5.

InChI:InChI=1/C6H8N2O2/c1-4-3-7-6(10)8(2)5(4)9/h3H,1-2H3,(H,7,10)

Upstream product

• 708-52-1 1,5-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carboxylic acid 
• 186581-53-3 diazomethane 
• 13251-16-6 l-Acetyl-5-methyluracil 
• 82387-33-5 (Z)-2-Methyl-3-(3-methyl-ureido)-acrylic acid methyl ester 
• 82387-32-4 (E)-2-Methyl-3-(3-methyl-ureido)-acrylic acid methyl ester 
• 84941-50-4 1,6-dihydro-1,5-dimethyl-2-(methylthio)-6-oxopyrimidine 
• 65-71-4 thymin 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 25902-91-4 2-methoxy-5-methylpyrimidin-4(3H)-one 
• 27460-05-5 3,5-dimethyl-2-methoxy-4-pyrimidinone 

Downstream Products

• 914086-93-4 C₁₉H₁₈N₂O₃ 

Relevant academic research and scientific papers

Repair of a Dimeric Azetidine Related to the Thymine-Cytosine (6 - 4) Photoproduct by Electron Transfer Photoreduction

Photolyases are intriguing enzymes that take advantage of sunlight to restore lesions like cyclobutane pyrimidine dimers or (6-4) photoproducts. This work focused on the photoreductive process responsible for splitting of the azetidine ring proposed to occur during (6-4) photoproduct repair at a thymine-cytosine sequence. A model compound formed by photocycloaddition between thymine and 6-azauracil has been designed to mimic the elusive azetidine intermediate. The photoinduced electron transfer process has been investigated by means of steady-state and time-resolved fluorescence using photosensitizers with oxidation potentials in the singlet excited state ranging from -3.3 to -2.1 V vs. SCE. Azetidine ring splitting and recovery of "repaired" bases were proven by HPLC analysis.

Investigation of the pathways of excess electron transfer in DNA with flavin-donor and oxetane-acceptor modified DNA hairpins

Oxetane is a potential intermediate that is enzymatically formed during the repair of (6-4) DNA lesions by special repair enzymes (6-4 DNA photolyases). These enzymes use a reduced and deprotonated flavin to cleave the oxetane by single electron donation.

HSAB-driven chemoselective N1-alkylation of pyrimidine bases and their 4-methoxy- or 4-acetylamino-derivatives

The lithium salts of the conjugated bases of 4-methoxy- and 4-acetylamino-2(1H)-pyrimidinones 1-3 undergo highly chemoselective N1-methylation or ethylation when treated with methyl- or ethylsulfate (hard electrophiles) in dry dioxane, while the use of DMF as solvent results in competitive O2-alkylation. Potassium salts of the same bases in DMF undergo prevalent O2-attack. Under the same conditions, a similar but less chemoselective behaviour is observed in alkylation of thymine and uracil, where some N3-attack occurs. This can be rationalised in terms of the HSAB principle.

HSAB driven chemoselectivity in alkylation of uracil derivatives. A high yielding preparation of 3-alkylated and unsymmetrically 1,3-dialkylated uracils

A qualitative hardness scale (N134) has been found for the conjugated bases of 2-methoxy-4(3H)-pyrimidinones 1-3 and applied to high yielding chemoselective N3 methylation, ethylation and benzylation reactions. Removal of the 2-methoxy group followed by a second alkylation affords unsymmetrically 1,3-disubstituted uracils.

N3-alkyl-2',5'-0-silylated-3'-spiro-thymidine derivatives

Nucleoside analogs possessing anti-HIV activity and having a 3'-spiro moiety and blocking groups at the 2'- and 5'-positions. The preferred species is shown in the structure below: STR1 wherein R is alkyl.

Oxidation of Thymines by Peroxosulfate Ions in Water

Oxidation of thymines by sodium peroxodisulfate in water at 85 deg C gave the corresponding 5-(hydroxymethyl)uracils and 5-formyluracils.The reaction may proceed via thymine cation radicals.On the other hand, oxidation of thymines by potassium peroxomonosulfate in water gave the corresponding cis-5,6-dihydroxy-5,6-dihydrothymines and 5-hydroxy-5-methylbarbituric acids.Furthermore, treatment of thymine with both potassium peroxomonosulfate and hydrogen peroxide in water gave cis-6-hydroperoxy-5-hydroxy-5,6-dihydrothymine.

SYNTHESIS OF METHYL 3-(N'-ALKYLUREIDO)-2-METHYL-2-PROPENOATES AND THEIR CYCLIZATION TO 3-ALKYL-5-METHYLURACILS

Stereoisomeric methyl 3-(N'-alkylureido)-2-methyl-2-propenoates (Ia-Id) were prepared by acid-catalyzed reaction of N-alkylureas (R = methyl, benzyl, isopropyl and tert-butyl) with methyl 3-methoxy-2-methyl-2-propenoate (III).Reaction of the ester III with N-tert-butylthiourea afforded the thioureides (E)-Ie and (Z)-Ie.On treatment with sodium methoxide in methanol, compounds Ia-Ic cyclized to the corresponding 3-alkyl-5-methyluracils IIa-IIc whereas compounds Id and Ie underwent only a base catalyzed E/Z isomerization with (E)-isomers predominating.