14181-46-5

Basic information

• Product Name: 1,3-dimethyl-5-hydroxymethyluracil
• CAS NO: 14181-46-5
• Molecular Weight: 170.168
• Mol File: 14181-46-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1,3-dimethyl-5-hydroxymethyluracil(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dimethyl-5-hydroxymethyluracil(14181-46-5)
• EPA Substance Registry System: 1,3-dimethyl-5-hydroxymethyluracil(14181-46-5)

Safety Data

• Hazardous Substances Data: 14181-46-5(Hazardous Substances Data)

Upstream product

• 3839-31-4 dimethyl(phenyl)silyllithium 
• 4869-46-9 1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde 
• 4401-71-2 1,3-dimethylthymine 
• 94820-37-8 1,3-Dimethyl-5-(1-phenyl-1H-tetrazol-5-ylsulfanylmethyl)-1H-pyrimidine-2,4-dione 
• 66224-66-6 adenine 

Relevant articles and documents

Reactivity of dimethylphenylsilyllithium toward 5- and 6-substituted 1,3-dimethyluracil derivatives

Dimethylphenylsilyllithium (PhMe2SiLi) reacts with 5-substituted 1,3-dimethyluracils by selective addition at the electrophilic C-6 position of the uracil ring to give the corresponding 6-dimethylphenylsilyl-5,6-dihydrouracil derivatives. The reaction of PhMe2SiLi with 6-substituted 1,3-dimethyluracils showed a different selectivity, and an unusual addition at the C-5 position was observed. This synthetic procedure appears to be an efficient entry to a new class of highly functionalized 5,6-dihydro-1,3-dimethyluraciIs characterized by the presence of a silicon substituent selectively introduced at the C-5 and C-6 positions of the uracil ring.

Oxidation of 1,3-dimethylthymine with oxone catalyzed by 5,10,15,20-tetrakis (4N-methylpyridiniumyl)porphyrinatomanganese (III) pentaacetate

The reaction of 1,3-dimethylthymine 2 with KHSO5 (oxone) catalyzed by 5, 10, 15, 20-tetrakis-(4N-methylpyridiniumyl)porphyrinatomanganese (III) pentaacetate 1 [T4MPyPMn (III) (OAc)5] in phosphate buffer gives 1,3-dimethyl-5-hydroxymethyluracil 3, 1,3-dimethyl-5-formyluracil 4, 1,3-dimethyluracil-5-carboxylic acid 5, cis-1,3-dimethylthymine-5,6-glycol 6 and 1,3,5-trimethyl-5-hydroxybarbituric acid 8 in different yields depending on the pH of the reaction medium. Oxidation of the 5-methyl group of 1,3-dimethylthymine to 1,3-dimethyl-5-hydroxymethyluracil 3, 1,3-dimethyl-5-formyluracil 4 and the corresponding acid 5 with oxone catalyzed by T4MPyPMn (III) (OAc)5 may be explained by hydrogen abstraction and recombination mechanism, whereas oxidation of 5,6-double bond of thymine to cis-1,3-dimethylthymine-5,6-glycol 6 and 1,3,5-trimethyl-5-hydroxybarbituric acid 8 may be explained either by electron transfer followed by oxygen atom transfer or by the involvement of hydroxy radicals.

Coupling of 1,3-Dimethylthymine and Adenine with Sodium Peroxodisulfate

Heating of a solution of 1,3-dimethylthymine and adenine in water containing sodium peroxodisulfate at 80 deg C resulted in the formation of their coupling products.