7417-28-9

Basic information

• Product Name: 2,4(1H,3H)-Pyrimidinedione, 5-hydroxy-6-methyl- (9CI)
• Synonyms: 2,4(1H,3H)-Pyrimidinedione, 5-hydroxy-6-methyl- (9CI);Oxymetacil;oxymethacil;2,4(1H,3H)-Pyrimidinedione, 5-hydroxy-6-methyl-;Nsc 70449;5-hydroxy-6-methylpyrimidine-2,4(1H,3H)-dione(SALTDATA: FREE);5-hydroxy-6-methylpyrimidine-2,4(1H,3H)-dione
• CAS NO: 7417-28-9
• Molecular Formula: C₅H₆N₂O₃
• Molecular Weight: 142.11274
• Product Categories: PYRIMIDINE
• Mol File: 7417-28-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 485.7°C at 760 mmHg
• Flash Point: 247.5°C
• Appearance: /
• Density: 1.453g/cm³
• Vapor Pressure: 4.67E-10mmHg at 25°C
• Refractive Index: 1.553
• CAS DataBase Reference: 2,4(1H,3H)-Pyrimidinedione, 5-hydroxy-6-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4(1H,3H)-Pyrimidinedione, 5-hydroxy-6-methyl- (9CI)(7417-28-9)
• EPA Substance Registry System: 2,4(1H,3H)-Pyrimidinedione, 5-hydroxy-6-methyl- (9CI)(7417-28-9)

Safety Data

• Hazardous Substances Data: 7417-28-9(Hazardous Substances Data)

Usage

General Description

2,4(1H,3H)-Pyrimidinedione, 5-hydroxy-6-methyl- (9CI) is a chemical compound with the molecular formula C5H6N2O3. It is a derivative of pyrimidine and has a hydroxyl group and a methyl group attached to the pyrimidine ring. 2,4(1H,3H)-Pyrimidinedione, 5-hydroxy-6-methyl- (9CI) is commonly used as a building block in organic synthesis and pharmaceutical research. It possesses potential biological activity and its derivatives have been investigated for their antiviral, anticancer, and antioxidant properties. Additionally, 2,4(1H,3H)-Pyrimidinedione, 5-hydroxy-6-methyl- (9CI) has been studied for its potential as a therapeutic agent for various medical conditions, making it a valuable chemical in the field of medicinal chemistry and drug development.

InChI:InChI=1/C5H6N2O3/c1-2-3(8)4(9)7-5(10)6-2/h8H,1H3,(H2,6,7,9,10)

Upstream product

• 1627-27-6 1,6-dimethylpyrimidine-2,4(1H,3H)-dione 
• 100531-71-3 5-isobutoxy-6-isobutoxymethyl-1H-pyrimidine-2,4-dione 
• 77-78-1 dimethyl sulfate 
• 124695-63-2 6-Methyluracil-5-sulfate 
• 626-48-2 6-Methyluracil 

Downstream Products

• 116319-09-6 4-Methyl-5-hydroxypyrimidine 3-Oxide 
• 116319-08-5 4-Methyl-5-hydroxypyrimidine 1-Oxide 
• 101257-87-8 4-Methyl-5-hydroxypyrimidine 
• 138192-68-4 3-N-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-5-hydroxy-6-methyl-1,2-dihydropyrimidine-2,4-dione 

Relevant articles and documents

A new synthesis of 5-hydroxy-6-methyluracil

Dehydration of 5,6-dihydro-5,6-dihydroxy-6-methyl- and 5,6-dihydro-5,6- dihydroxy-1,3,6-trimethyl-uracil in 0.4 M aqueous sulfuric acid gives 5-hydroxy-6-methyl- and 5-hydroxy-1,3,6-trimethyluracil in quantitative yields. Two possible mechanisms have been examined using the mPW1k/6-311+G(2df,2pd)// mPW1k/6-31+G(d,p) method for the transformation of methylated and non-methylated 5,6-dihydro-5,6-dihydroxy-6-methyluracils into the corresponding 5-hydroxy-6-methyluracils. The first is a hydride C5-C6 shift occurring in concert with the loss of a water molecule and formation of the corresponding protonated 5,6-dihydro-5-oxo-6-methyluracils. The second is an acid-catalyzed dehydration reaction to yield 5-hydroxy-6-methyluracils. The calculations demonstrated that the second pathway was energetically most favorable.

SYNTHESIS OF BISURACIL SULFOLANE DERIVATIVES

Bisuracil sulfolane derivatives have been synthesized using the silyl method of nucleoside synthesis in the presence of SnCl4.The necessary starting materials were 5-hydroxy-6-methyluracil (prepared by oxidation of 6-methyluracil with ammonium persulfate in aqueous medium) and trans-3,4-diacetoxysulfolane (prepared from trans-3,4-dihydroxysulfolane).The structures of the bisuracil sulfolane derivatives were established based on their spectral data and elemental analysis.