1194-22-5

Basic information

• Product Name: 4,6-Dihydroxy-2-methylpyrimidine
• Synonyms: 4(1H)-Pyrimidinone, 6-hydroxy-2-methyl- (8CI,9CI);4-hydroxy-2-methyl-1H-pyrimidin-6-one;4(1H)-PyriMidinone, 6-hydroxy-2-Methyl-;NSC 9317;6-hydroxy-2-methyl-3H-pyrimidin-4-one;6-hydroxy-2-methyl-4(1H)-Pyrimidinone
• CAS NO: 1194-22-5
• Molecular Formula: C₅H₆N₂O₂
• Molecular Weight: 126.11334
• Product Categories: PYRIMIDINE;Heterocycle-Pyrimidine series
• Mol File: 1194-22-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 314.4 °C at 760 mmHg
• Flash Point: 143.9 °C
• Appearance: /
• Density: 1.44 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.46±0.10(Predicted)
• CAS DataBase Reference: 4,6-Dihydroxy-2-methylpyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-Dihydroxy-2-methylpyrimidine(1194-22-5)
• EPA Substance Registry System: 4,6-Dihydroxy-2-methylpyrimidine(1194-22-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 1194-22-5(Hazardous Substances Data)

Usage

Description

4,6-Dihydroxy-2-methylpyrimidine is a pyrimidine derivative with the molecular formula C5H6N2O2. It features a pyrimidine ring with two hydroxyl groups and a methyl group attached, contributing to its chemical properties and potential applications. 4,6-Dihydroxy-2-methylpyrimidine is recognized for its antioxidant properties and is utilized as a precursor in the synthesis of pharmaceuticals and agrochemicals, as well as in the development of nucleoside analogs for antiviral and anticancer drugs.

Uses

Used in Pharmaceutical Industry:
4,6-Dihydroxy-2-methylpyrimidine is used as a precursor for the synthesis of various pharmaceuticals due to its ability to be incorporated into complex molecular structures, enhancing the development of new therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 4,6-Dihydroxy-2-methylpyrimidine serves as a starting material for the creation of agrochemicals, potentially contributing to the development of novel pesticides or herbicides.
Used in Antioxidant Formulations:
4,6-Dihydroxy-2-methylpyrimidine is used as an antioxidant in various applications, capitalizing on its ability to combat oxidative stress, which is beneficial in the formulation of health supplements and cosmetics.
Used in Nucleoside Analog Synthesis:
4,6-Dihydroxy-2-methylpyrimidine is utilized as a key building block in the synthesis of nucleoside analogs, which are crucial in the development of antiviral and anticancer medications, targeting specific biological processes to treat diseases effectively.
Overall, 4,6-Dihydroxy-2-methylpyrimidine's multifaceted applications in different industries underscore its importance in modern chemical and pharmaceutical research and development.

Upstream product

• 124-42-5 acetamidine hydrochloride 
• 105-53-3 diethyl malonate 

Downstream Products

• 145250-81-3 2,2-dinitroethene-1,1-diamine 
• 129207-40-5 6-benzoylamino-4-hydroxy-2-methyl-7H-pyrano<2,3-d>pyrimidin-7-one 
• 1338327-19-7 6-(4-bromophenyl)-4-chloro-2-methyl-7,8-dihydropyrimido[5,4-f][1,4]oxazepin-5(6H)-one 
• 1338327-20-0 N-(4-bromophenyl)-4,6-dichloro-N-(2-hydroxyethyl)-2-methylpyrimidine-5-carboxamide 
• 1338327-21-1 N-(4-bromophenyl)-N-(2-(tert-butyldimethylsilyloxy)ethyl)-4,6-dichloro-2-methylpyrimidine-5-carboxamide 
• 53925-27-2 2-methyl-4,6-dihydroxy-5-nitropyrimidine 
• 197802-86-1 2-methyl-5-nitro-6-(2,4,6-trimethyl-phenylamino)-3H-pyrimidin-4-one 
• 169883-27-6 4-N-<2-bromo-4-(1-methylethyl)phenyl>-6-chloro-2-methylpyrimidine-4,5-diamine 
• 197802-88-3 6-chloro-2-methyl-N⁴-(2,4,6-trimethyl-phenyl)-pyrimidine-4,5-diamine 
• 175140-70-2 4-N-(2,4,6-trimethylphenyl)-6-chloro-2-methyl-5-nitropyrimidin-4-amine 
• 82779-50-8 4,6-dichloro-2-methyl-5-nitropyrimidine 
• 1026887-85-3 2-Methyl-5-nitro-4-piperidin-1-yl-6-[(Z)-2-pyrrolidin-1-yl-2-(3,4,5-trifluoro-phenyl)-vinyl]-pyrimidine 
• 1026561-09-0 2-Methyl-5-nitro-4-piperidin-1-yl-6-[(Z)-2-pyrrolidin-1-yl-2-(4-trifluoromethyl-phenyl)-vinyl]-pyrimidine 
• 1027393-84-5 2-Methyl-5-nitro-4-piperidin-1-yl-6-[(Z)-2-pyrrolidin-1-yl-2-(2-trifluoromethyl-phenyl)-vinyl]-pyrimidine 

Relevant articles and documents

An efficient and convenient synthesis of 4,6-Dichloro-2-methyl-5- nitropyrimidine

A convenient synthesis of 4, 6-dihydro-2-methyl-pyrimidine can be obtained by cyclization reaction of acetamidine hydrochloride and diethyl malonate in the presence of sodium methoxide for a 91.2 % yield. 4, 6-Dihydro-2-methyl-5- nitropyrimidine can be achieved by nitration under the mixed acids of nitric acid, trichloroacetic acid and acetic acid in an 88.3 % yield and then the chlorination using phosphorus oxytrichloride can afford 4, 6-dichloro-2-methyl- 5-nitropyrimidine with an 82.6 % yield.

Phenyl and Diaryl Ureas with Thiazolo[5,4-d]pyrimidine Scaffold as Angiogenesis Inhibitors: Design, Synthesis and Biological Evaluation

Angiogenesis is crucial for tumor growth and inhibition of angiogenesis has been regarded as a promising approach for cancer therapy. Vascular endothelial growth factor receptor-2 (VEGFR-2) is an important factor in angiogenesis. In this work, a novel series of thiazolo[5,4-d]pyrimidine derivatives inhibiting angiogenesis were rationally designed and synthesized. Their inhibitory activities against human umbilical vein endothelial cells (HUVEC) were investigated in vitro. 1-(4-Fluorophenyl)-3-{4-[(5-methyl-2-phenyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl)amino]phenyl}urea (19b) and 1-(3-Fluorophenyl)-3-{4-[(5-methyl-2-phenyl[1,3]thiazolo[5,4-d]pyrimidin-7-yl)amino]phenyl}urea (19g) exhibited the most potent inhibitory effect on HUVEC proliferation (IC50=12.8 and 5.3 μm, respectively). Compound 19g could inhibit the migration of human umbilical vein endothelial cells. These results support the further investigation of these compounds as potent anticancer agents.

A convenient synthesis of 5-arylamino-4H-pyran-4-ones using palladium-catalyzed amination

A concise approach to 5-arylamino-4H-pyran-4-ones is described via palladium-catalyzed amination reaction. The methodology involved in this Letter is based on protection/deprotection protocols and on manipulation of the 5-hydroxy group of readily available kojic acid. It would provide a new entry to a range of 5-arylamino-4H-pyran-4-ones via Buchwald-Hartwig-type amination reaction on 4H-pyran-4-one unit.