5661-00-7

Upstream product

• 83942-13-6 4-chloro-6,7-dihydro-5H-cyclopenta[d]pyrimidine 
• 2611-03-2 2-chlorocyclopent-1-ene-1-carbaldehyde 
• 77287-34-4 formamide 
• 120-92-3 cyclopentanone 
• 290-87-9 1,3,5-Triazine 
• 7148-07-4 1-pyrrolidinocyclopent-1-ene 
• 17758-33-7 3-methyl-5-nitro-4(3H)-pyrimidinone 
• 936-52-7 1-(N-morpholino)cyclopent-1-ene 
• 3473-63-0 formamidine acetic acid 

Downstream Products

• 65242-18-4 2-amino-3-cyano-5,6-trimethylenepyridine 

Relevant academic research and scientific papers

Reaction of Aldehydes/Ketones with Electron-Deficient 1,3,5-Triazines Leading to Functionalized Pyrimidines as Diels-Alder/Retro-Diels-Alder Reaction Products: Reaction Development and Mechanistic Studies

Catalytic inverse electron demand Diels-Alder (IEDDA) reactions of heterocyclic aza-dienes are rarely reported since highly reactive and electron-rich dienophiles are often found not compatible with strong acids such as Lewis acids. Herein, we disclose that TFA-catalyzed reactions of electron-deficient 1,3,5-triazines and electron-deficient aldehydes/ketones can take place. These reactions led to highly functionalized pyrimidines as products in fair to good yields. The reaction mechanism was carefully studied by the combination of experimental and computational studies. The reactions involve a cascade of stepwise inverse electron demand hetero-Diels-Alder (ihDA) reactions, followed by retro-Diels-Alder (rDA) reactions and elimination of water. An acid was required for both ihDA and rDA reactions. This mechanism was further verified by comparing the relative reactivity of aldehydes/ketones and their corresponding vinyl ethers in the current reaction system.

Direct access to pyrimidines through organocatalytic inverse-electron-demand Diels-Alder reaction of ketones with 1,3,5-triazine

An organocatalytic inverse-electron-demand Diels-Alder reaction of ketones with 1,3,5-triazine through enamine catalysis has been developed. This method could furnish 4,5-disubstituted pyrimidines in good yields and high levels of regioselectivities.

HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF

Provided herein are thiophene compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.

Mechanistic aspect of ring transformations in the reaction of 5-nitro-4-pyrimidinone with acetophenone derivatives and cycloalkanones depending on the electron density/ring size of the ketone

3-Methyl-5-nitro-4-pyrimidinone undergoes two kinds of nucleophilic type ring transformations upon treatment with cycloalkanones in the presence of ammonium acetate, which affords 4,5-disubstituted pyrimidines and 5,6-disubstituted 3-nitro-2-pyridones. In order to improve the synthetic utility of this reaction, it is necessary to control the regioselectivity of these ring transformations. In the present work, we performed DFT calculation to realize the selectivity of two ring transformation products. In cases of adduct intermediates derived from cyclohexanone and cyclooctanone, the 2-attack proceeds preferably to give condensed pyrimidines. On the other hand, the adduct intermediate derived from cycloheptanone undergoes the 4-attack predominantly to afford condensed nitropyridone.

One-step synthesis of 4,5-disubstituted pyrimidines using commercially available and inexpensive reagents

4,5-Disubstituted pyrimidines are synthesized from the corresponding ketone in one-step using inexpensive reagents (formamidine acetate, n-propanol, heat). Contrasted to other methods, this process appears quite amenable to large-scale use in industrial settings.

Palladium-catalysed synthesis of pyrimidines

Satisfactory yields of 4-substituted pyrimidines and bicyclic pyrimidines are produced from α-methyl or α-methylene ketones when reacted with formamide and tetrakis(triphenylphosphine)palladium(0) or a 1:2 mixture of palladium(II) acetate and triphenylphosphine as catalysts. Under the same reaction conditions pyridines or imidazole are formed from 1,3- or 1,2-diketones.

Two ring transformations of 3-methyl-5-nitropyrimidin-4(3H)-one for the construction of azaheterocycles

The reaction of 3-methyl-5-nitropyrimidin-4(3H)-one with ketones in the presence of NH3 afforded 4,5-disubstituted pyrimidines 5. Use of ammonium acetate instead of NH3 as the nitrogen source caused another ring transformation giving 5,6-disubstituted 3-nitro-2-pyridones 8 as well as 5. Pyrimidinone 1 behaved as an activated diformylamine 6 in the former reaction and as the synthetic equivalent of α-nitroformylacetic acid 9 in the latter case. The ratio of 5 and 8 produced when using NH4OAc varied with solvent. The reaction in acetic acid predominantly afforded pyrimidine 5, but in methanol the reaction afforded pyridone 8. The two types of ring transformations presented here are novel methods for the preparations of azaheterocycles.

Novel ring transformation of nitropyrimidinone; synthetic equivalent of α-nitroformylacetic acid

3-Methyl-5-nitropyrimidin-4(3H)-one reacts with ketones in the presence of ammonium salts to afford disubstituted pyrimidines and disubstituted 3-nitro-2-pyridones in a novel ring transformation reaction; nitropyrimidinone behaves as an activated diformylamine in the former case, and as a synthetic equivalent of α-nitroformylacetic acid in the latter case.

Intermediates for making N-aryl and N-heteroarylamide and urea derivatives as inhibitors of acyl coenzyme A: cholesterol acyl transferase (ACAT)

Compounds of the formula STR1 wherein R21 and R22 are as defined in the specification which are intermediates useful in the preparation of compounds of the formula STR2 and the pharmaceutically acceptable salts thereof, wherein Q and R1 are as defined in the specification. The compounds of formula I are inhibitors of acyl coenzyme A: cholesterol acyltransferase (ACAT) and are useful as hypolipidemic and antiatherosclerosis agents.

NOVEL SYNTHESIS OF SUBSTITUTED PYRIMIDINES: A RING TRANSFORMATION OF 3-METHYL-5-NITROPYRIMIDIN-4(3H)-ONE

A novel ring transformation of 3-methyl-5-nitropyrimidin-4(3H)-one with ketones in the presence of ammonia was found to be an elegant method for synthesizing 5,6-disubstituted pyrimidines.Tetrahydroquinazoline was readily obtained in good yields when cyclohexanone was employed as a substrate.The present reaction was applicable to cyclopentanone, acetophenone and p-nitroacetophenone to give corresponding pyrimidine derivatives.