130161-46-5

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-Phenylpyrimidine-5-carboxaldehyde is utilized as a key building block in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows for the creation of diverse molecules with potential therapeutic and pesticidal activities.
Used in Drug Discovery and Development:
As a target for research in drug discovery and development, 2-Phenylpyrimidine-5-carboxaldehyde is employed for its potential antitumor and antiviral properties. Its reactivity and structural features make it a valuable intermediate for the design and synthesis of new drugs aimed at treating cancer and viral infections.
Used in Organic Chemistry Research:
2-Phenylpyrimidine-5-carboxaldehyde is also used in organic chemistry as a valuable intermediate for studying reaction mechanisms and developing new synthetic methodologies. Its presence in various chemical reactions can provide insights into the behavior of heterocyclic compounds and contribute to the advancement of organic synthesis techniques.

InChI:InChI=1/C11H8N2O/c14-8-9-6-12-11(13-7-9)10-4-2-1-3-5-10/h1-8H

Upstream product

• 18655-47-5 triformylmethane 
• 1670-14-0 benzamidine monohydrochloride 
• 2009-81-6 2-dimethylaminomethylene-1,3-bis(dimethylimonio)propane diperchlorate 
• 618-39-3 benzamidin 
• 90905-31-0 2-(methylsulfanyl)pyrimidine-5-carbaldehyde 
• 98-80-6 phenylboronic acid 
• 886531-62-0 (2-phenylpyrimidin-5-yl)methanol 
• 38696-20-7 2-phenyl-5-bromopyrimidine 
• 107-31-3 Methyl formate 

Downstream Products

• 545421-44-1 (2E)-3-(2-Phenyl-5-pyrimidinyl)-2-propen-1-ol 
• 886531-62-0 (2-phenylpyrimidin-5-yl)methanol 
• 1361000-90-9 (E)-2-(5-fluoro-1-((2-phenylpyrimidin-5-yl)methylene)-1H-inden-3-yl)acetic acid 
• 1192251-78-7 6-(methylsulfonyl)-2-(2-phenylpyrimidin-5-yl)-1H-benzimidazole 

Relevant academic research and scientific papers

Synthesis of Soai Type 2-Arylpyrimidine-5-carbaldehydes through Desulfurative Cross-Coupling with Arylboronic Acids

A two-step synthesis of 2-arylpyrimidine-5-carbaldehydes, which are of relevance as substrates for Soai's asymmetric autocatalysis, was realized by exploiting a hidden threefold symmetry in the target core structure. Condensation of Arnold's C 3-symmetric vinamidinium cation with S-methylisothiouronium sulfate provides 2-methylsulfanyl-pyrimidine-5-carbaldehyde; introduction of aryl groups at C-2 of the latter was accomplished by a Liebeskind-Srogl palladium-catalyzed desulfurative (de-methylsulfanylative) coupling with aryl boronic acids to obtain the target compounds 1 (14 examples, 60-95 % yield). 2-Arylpyrimidine-5-carbaldehydes, which are of relevance as substrates in Soai's asymmetric autocatalysis, are prepared through Liebeskind-Srogl coupling of aryl boronic acids with 2-methylthiopyrimidine-5-carbaldehyde; the latter is obtained in a hydrolytic condensation of two symmetric amidinium salts.

NOVEL SUBSTITUTED HETEROAROMATIC COMPOUNDS AS INHIBITORS OF STEAROYL-COENZYME A DELTA-9 DESATURASE

Substituted heteroaromatic compounds of structural formula I are inhibitors of stearoyl-coenzyme A delta-9 desaturase. The compounds of the present invention are useful for the prevention and treatment of conditions related to abnormal lipid synthesis and metabolism, including cardiovascular disease, such as atherosclerosis; obesity; Type 2 diabetes; insulin resistance; hyperglycemia; Metabolic Syndrome; neurological disease; cancer; and liver steatosis. Formula (I).

LACTAM COMPOUNDS AND MEDICINAL USE THEREOF

An agent for increasing the sugar-transporting capacity and an agent for preventing and/or treating diabetes, diabetic peripheral neuropathy, diabetic nephropathy, diabetic retinopathy, diabetic macroangiopathy, impaired glucose tolerance or adiposis, which contains a lactam compound or a pharmaceutically acceptable salt thereof as the active ingredient.

6-O-acyl ketolide antibacterials

6-O-Acyl ketolide antibacterials of the formula: wherein R1, R2, R3, R4, W, X, X′, Y, and Y′ are as described herein and in which the substituents have the meaning indicated in the description. These compounds are useful as antibacterial agents.

Shock sensitivity of a vinamidinium bis-perchlorate reagent and demonstration of a lower energy alternative

'Vinamidinium' bis-perchlorate salt 1 (2-dimethylaminomethylene-1,3-bis(dimethylimmonio)-propane bis-perchlorate) was found to possess remarkably high thermal energy as well as significant shock sensitivity. A reported method for preparation of 2,5-disubstituted pyrimidines with 1 was of interest, and we found that the corresponding bis-tetrafluoroborate salt 2 was equally effective in this transformation, while possessing significantly lower thermal energy.

Formation of Pyrimidine-5-carboxaldehydes, 1-Aminoethylene-2,2-dicarboxaldehyde and 2-Amino-4-anilino-1,3,5-triazine from Triformylmethane and Amidines

Triformylmethane (1) reacted with benzamidine, guanidine and S-methylisothiourea to give the corresponding 2-substituted pyrimidines-5-carboxaldehydes.However reactions of 1 with acetamidine (or formamidine) and phenylbiguanide gave the unexpected 1-aminoethylene-2,2-dicarboxaldehyde (5) and 2-amino-4-anilino-1,3,5-triazine (9), respectively.

An Alternative Preparation of the 2-Dimethylaminomethylene-1,3-bis(dimethylimminio)propane Salt from Phosphonoacetic Acids and Some Applications in Heterocyclic Synthesis

An alternative preparation of a 2-iminovinamidinium salt from phosphonoacetic acids is described along with its application to the synthesis of 5-formylpyrimidines and masked 4-formylpyrazoles.

DIRECT SYNTHESIS OF 2-SUBSTITUTED 5-FORMYLPYRIMIDINES AND RING TRANSFORMATION OF THEIR PHENYLHYDRAZONES INTO 4-FORMYL-1-PHENYLPYRAZOLE

Triformylmethane (1) reacted with benzamidine, guanidine and S-methylisothiourea to give 2-substituted 5-formylpyrimidines (2a-c), whose phenylhydrazones (3a-c) readily underwent ring transformation into 4-formyl-1-phenylpyrazole (4) on heating in acidic methanol.

Direct syntheses of pyrazole-4-carbaldehydes and pyrimidine-5-carbaldehydes starting from triformylmethane.

Triformylmethane is transformed into the pyrazole-4-carbaldehydes 2, 4, 6, 7, 9, 11 and the pyrazole-4-carbaldehydes 8, 10, 12 by corresponding hydrazines, and into the pyrimidine-5-carbaldehydes 13, 14, 15 by appropriate amidines.