10098-27-8

Basic information

• Product Name: 5-hydroxy-6-methylpyrimidine-2,4(1H,3H)-dione
• Synonyms: 2,4(1H,3H)-pyrimidinedione, 5-hydroxy-6-methyl-; 5-Hydroxy-6-methylpyrimidine-2,4(1H,3H)-dione
• CAS NO: 10098-27-8
• Molecular Formula: C₅H₆N₂O₃
• Molecular Weight: 142.1127
• Mol File: 10098-27-8.mol

Chemical Properties

• Boiling Point: 485.7°C at 760 mmHg
• Flash Point: 247.5°C
• Density: 1.453g/cm³
• Vapor Pressure: 4.67E-10mmHg at 25°C
• Refractive Index: 1.553
• CAS DataBase Reference: 5-hydroxy-6-methylpyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-hydroxy-6-methylpyrimidine-2,4(1H,3H)-dione(10098-27-8)
• EPA Substance Registry System: 5-hydroxy-6-methylpyrimidine-2,4(1H,3H)-dione(10098-27-8)

Safety Data

• Hazardous Substances Data: 10098-27-8(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 101257-87-8 4-Methyl-5-hydroxypyrimidine 
• 116319-08-5 4-Methyl-5-hydroxypyrimidine 1-Oxide 
• 116319-09-6 4-Methyl-5-hydroxypyrimidine 3-Oxide 

Relevant articles and documents

4-METHYL-5-HYDROXYPYRIMIDINE AND ITS N-OXIDES: SYNTHESIS AND INVESTIGATION OF THE REACTIVITIES IN ELECTROPHILIC SUBSTITUTION

A new more accessible method for the synthesis of 4-methyl-5-hydroxypyrimidine is proposed; its 1- and 3-oxides were obtained.An attempt was made to evaluate the reactivities of the individual positions of the heterocyclic ring of pyrimidine and its 3-oxide in aminomethylation.

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.

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.