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

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

Uses

Used in Pharmaceutical Industry:
3-(DIMETHYLAMINO)-1-(2-PYRAZINYL)-2-PROPEN-1-ONE is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new medicinal compounds.
Used in Organic Synthesis:
In the field of organic synthesis, 3-(DIMETHYLAMINO)-1-(2-PYRAZINYL)-2-PROPEN-1-ONE is used as a reagent in chemical reactions, facilitating the creation of a variety of organic compounds.
Used in Chemical Research:
3-(DIMETHYLAMINO)-1-(2-PYRAZINYL)-2-PROPEN-1-ONE is used as a building block in chemical research for the production of various organic compounds, aiding in the advancement of chemical knowledge and innovation.

Upstream product

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

Downstream Products

• 926037-48-1 Radotinib 
• 1344018-86-5 C₁₀H₆N₄S 
• 641615-37-4 N-(2-methyl-5-nitrophenyl)-4-(pyrazinyl)-2-pyrimidine-amine 
• 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.

Discovery and structure-activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors

Current treatment for hepatitis C is barely satisfactory, there is an urgent need to develop novel agents for combating hepatitis C virus infection. This study discovered a new class of thieno[2,3-b]pyridine derivatives as HCV inhibitors. First, a hit compound characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. And then, structure activity relationship study of the hit compound led to the discovery of several potent compounds without obvious cytotoxicity in vitro (12c, EC50 = 3.3 μM, SI >30.3, 12b, EC50 = 3.5 μM, SI >28.6, 10l, EC50 = 3.9 μM, SI >25.6, 12o, EC 50 = 4.5 μM, SI >22.2, respectively). Although the mechanism of them had not been clearly elucidated, our preliminary optimization of this class of compounds had provided us a start point to develop new anti-HCV agents.

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.

Synthesis and antibacterial activity of novel 5-(heteroaryl)isoxazole derivatives

The synthesis, characterization and antibacterial activity of novel isoxazole derivatives were reported. 3-Di (alkylamino)acryloalkanones were prepared and used as synthons to get the target isoxazole derivatives via reaction with hydroxylamine hydrochloride or hydroxylamine-O-sulphonic acid.

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.

N-PHENYL-2-PYRIMIDINE-AMINE DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF

The present invention relates to a novel N-phenyl-2-pyrimidine-amine derivative represented by the above formula (1) and its salt showing a superior effect on cancer in warm-blooded animals, such as lung cancer, gastric cancer, colon cancer, pancreatic cancer, hepatoma, prostatic cancer, breast cancer, chronic or acute leukemia, hematologic malignancy, encephalophyma, bladder cancer, rectal cancer, cervical cancer, lymphoma, etc. The present invention also relates to a process for preparing the compound, and to a pharmaceutical composition for the treatment of the above various diseases, which comprises an effective amount of the compound as an active ingredient together with pharmaceutically acceptable inert carriers.

AMIDE DERIVATIVE

The present invention provides an amide derivative represented by the following general formula (1): wherein R1 represents a saturated cyclic amino group, R2 represents alkyl, halogen or haloalkyl, R3 represents hydrogen or halogen, Het 2 represents pyridyl or pyrimidinyl, and Het 1 represents a group of the formula [6], or a salt thereof, and a pharmaceutical composition comprising the same as an active ingredient. The compound of the present invention is useful as a BCR-ABL tyrosine kinase inhibitor.

Synthesis of some new 6,8-disubstituted 7,8-dihydropyrimido[2,3:4,3] pyrazolo[1,5-a]pyrimidines and 6,7,8-trisubstituted pyrimido[2,3:4,3]pyrazolo[1, 5-a]pyrimidine derivatives

Cyclization of 5-cyano-1,6-dihydro-4-methyl-2-phenyl-6-thioxopyrimidine 4 with excess of 85% hydrazine hydrate afforded the 3-amino-4-methyl-6- phenylpyrazolo[3,4-d]pyrimidine 5, which can react with appropriate Mannich base derivatives 13a-c and chalcones 27a,b to yield the corresponding 6,8-disubstituted 7,8-dihydropyrimido[2,3:4,3]pyrazolo[1,5-a]pyrimidines 15a-c and 30a,b, respectively. On the other hand, the 6,7,8-trisubstituted pyrimido[2,3:4,3]pyrazolo[1,5-a]pyrimidine derivatives 8a-g, 20a-e, 36 and 38 were obtained by treatment of compound 5 with appropriate 1,3-diketones 6a-g, 3-dimethylamino-1-(substituted)prop-2-enones 18a-e, 3-aminocrotononitrile 3, and ethoxymethylenemalononitrile 37 under acidic condition, respectively.