111781-53-4

Basic information

• Product Name: 3-(DIMETHYLAMINO)-1-(2-PYRAZINYL)-2-PROPEN-1-ONE
• Synonyms: 3-(DIMETHYLAMINO)-1-(2-PYRAZINYL)-2-PROPEN-1-ONE;3-(DIMETHYLAMINO)-1-(PYRAZIN-2-YL)PROP-2-EN-1-ONE
• CAS NO: 111781-53-4
• Molecular Formula: C₉H₁₁N₃O
• Molecular Weight: 177.2
• Mol File: 111781-53-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 131-133°
• Boiling Point: 288.1±40.0 °C(Predicted)
• Appearance: /
• Density: 1.122±0.06 g/cm3(Predicted)
• PKA: 5.88±0.70(Predicted)
• CAS DataBase Reference: 3-(DIMETHYLAMINO)-1-(2-PYRAZINYL)-2-PROPEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(DIMETHYLAMINO)-1-(2-PYRAZINYL)-2-PROPEN-1-ONE(111781-53-4)
• EPA Substance Registry System: 3-(DIMETHYLAMINO)-1-(2-PYRAZINYL)-2-PROPEN-1-ONE(111781-53-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 111781-53-4(Hazardous Substances Data)

Usage

General Description

3-(Dimethylamino)-1-(2-pyrazinyl)-2-propen-1-one is a chemical compound with the molecular formula C10H12N2O. It is a yellow to orange crystalline solid that is used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. It is also used as a reagent in chemical reactions and as a building block for the production of various organic compounds. The chemical is flammable and should be handled and stored with care in a well-ventilated area, away from sources of ignition and heat. It is important to follow safety and handling guidelines when working with this compound.

Upstream product

• 22047-25-2 acetylpyrazine 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 

Downstream Products

• 641615-37-4 N-(2-methyl-5-nitrophenyl)-4-(pyrazinyl)-2-pyrimidine-amine 
• 1344018-86-5 C₁₀H₆N₄S 
• 926037-48-1 Radotinib 
• 641615-38-5 4-methyl-N*3*-(4-pyrazin-2-yl-pyrimidin-2-yl)-benzene-1,3-diamine 

Relevant articles and documents

An optimized approach in the synthesis of imatinib intermediates and analogues

We revisited the classical synthetic procedure for imatinib synthesis providing an improved and optimized approach in the preparation of a series of new imatinib analogues. The proposed methodology effectively overcomes certain problematic steps, saves time and labor, provides a very high yield and purity and has the potential to be used for the synthesis of many analogues. The formation of the desired guanidine salt 4, one of the key steps to the imatinib synthesis, was proceeded almost quantitatively by the reaction of the hydrochloride of the suitable aniline 3 with excess of molten cyanamide, without any solvent. Pure arylamine intermediates 6a-d were obtained quantitatively in a short reaction time after reduction of the nitro group of the intermediate pyrimidines 5a-d with hydrogen over the Adam's catalyst. In addition, the application of this optimized approach can be extended in the synthesis of nilotinib and its analogues intermediates.

Synthesis and antimicrobial activity of novel 7-(Heteroaryl)-1,2,4- triazolo[1,5-a]-pyrimidine derivatives

The synthesis, characterization and antimicrobial activity of novel 1,2,4-triazolo[1,5-a]pyrimidines have been reported. The compounds were prepared by acid catalyzed condensation of 3-amino-1,2,4-triazole with 3-(dialkylamino)acryloalkanone.

A facile total synthesis of imatinib base and its analogues

Imatinib and its analogues were successfully synthesized by an improved method in 19.5-46.2% total yield of six main steps. Pyrimidinyl amine was prepared by the reaction of enaminone and guanidine nitrate without the use of a toxic cyanamide. N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl) pyrimidin-2-amine as a key intermediate for the synthesis of imatinib was prepared by coppercatalyzed iV-arylation of heteroarylamme in 82% yield. The copper salts were used instead of the expensive palladium compounds in this C-N bond-forming reaction. The intermediate nitro compound was reduced by a N2H 4.H2O/FeCl3/C system using water as a solvent in good yield.