695-87-4

Usage

Uses

Used in Pharmaceutical Industry:
4(1H)-Pyrimidinone, 5-methoxy(9CI) is used as a key intermediate in the synthesis of Oxazolylphenyl alkylcarbamates, which are known as FAAH (fatty acid amide hydrolase) inhibitors. FAAH inhibitors have potential therapeutic applications in the treatment of various neurological disorders, such as anxiety, depression, and chronic pain, due to their ability to modulate the endocannabinoid system.
In the synthesis of Oxazolylphenyl alkylcarbamates, 4(1H)-Pyrimidinone, 5-methoxy(9CI) plays a crucial role in the formation of the desired molecular structure, which is responsible for the inhibitory activity against FAAH. This makes it an essential component in the development of novel and effective therapeutic agents targeting the endocannabinoid system.

Upstream product

• 31458-33-0 5-methoxypyrimidine 

Downstream Products

• 51793-91-0 5-methoxy-3H-pyrimidine-4-thione 
• 71133-26-1 4,5-dimethyoxypyrimidine 
• 31458-33-0 5-methoxypyrimidine 
• 695-85-2 4-chloro-5-methoxy-pyrimidine 
• 695-86-3 amino-4 methoxy-5 pyrimidine 
• 151140-96-4 avitriptan 
• 141071-86-5 5-methoxy-4-piperazin-1-yl-pyrimidine 

Relevant academic research and scientific papers

Reactions of benzonitrile oxide with methoxypyrimidines and pyrimidones

Methoxypyrimidines preferentially add to benzonitrile oxide to give cycloadducts to their C=N double bonds. These, however, lose benzonitrile affording the corresponding pyrimidones. Cycloadditions to their C=C double bonds take place to a very low extent, and products generally undergo a ring opening process which affords the corresponding oximes. Pyrimidones preferentially give addition products to their nitrogen atoms, and only in the case of 4-pyrimidone, the cycloadduct to its C=C double bond was isolated.

Chemistry of Pyrimidine. 2. Synthesis of Pyrimidine N-Oxides and 4-Pyrimidinones by Reaction of 5-Substituted Pyrimidines with Peracids. Evidence for Covalent Hydrates as Reaction Intermediates

The reaction of 5-substituted pyrimidines with peracids has been found to take divergent pathways depending on the presence or absence of a strong acid.Reaction of 5-bromo- (1) or 5-methoxypyrimidine (6) with m-chloroperbenzoic acid afforded the corresponding N-oxides in 29percent and 70percent yields, respectively.The formation of an N-oxide was not observed when either 1 or 6 was treated with 40percent peracetic acid in the presence of 1 equiv of sulfuric acid.In the case of 1, the product was 5-bromo-5(3H)-pyrimidinone (3), formed in 70percent yield.From 6, two products, 5-methoxy-4-(3H)-pyrimidinone (8) and 4(5)-carbomethoxyimidazole (9), were formed in a combined yield of 70percent (3:2 ratio of 8 to 9).The N-oxides were demonstrated to be stable to the above reaction conditions and are therefore not intermediates in the formation of 3, 8, or 9.Evidence for the existence of covalent hydrates makes it reasonable to suggest their formation as reaction intermediates.