143870-65-9

Upstream product

• 98-88-4 benzoyl chloride 
• 747376-89-2 C₉H₁₆N₂O₃ 
• 630-19-3 pivalaldehyde 
• 131791-76-9 cis-2-tert-butyl-6(S)-potassium carboxylate-perhydropyrimidin-4-one 

Downstream Products

• 143870-66-0 1-benzoyl-2(S)-tert-butyl-2,3-dihydro-4(1H)-pyrimidin-4-one 
• 183182-00-5 1-benzoyl-(2S)-tert-butyl-3-methyl-(5R)-benzylperhydropyrimidin-4-one 
• 183182-04-9 (2S,5S)-1-Benzoyl-5-benzyl-2-tert-butyl-3-methyl-tetrahydro-pyrimidin-4-one 
• 183181-99-9 1-benzoyl-2(S)-tert-butyl-3-methyl-5(R)-n-hexylperhydropyrimidin-4-one 
• 183182-03-8 (2S,5S)-1-Benzoyl-2-tert-butyl-5-hexyl-3-methyl-tetrahydro-pyrimidin-4-one 
• 183181-98-8 (2S,5R)-1-Benzoyl-5-butyl-2-tert-butyl-3-methyl-tetrahydro-pyrimidin-4-one 
• 183182-02-7 (2S,5S)-1-Benzoyl-5-butyl-2-tert-butyl-3-methyl-tetrahydro-pyrimidin-4-one 
• 183182-01-6 (2S,5S)-1-Benzoyl-2-tert-butyl-3,5-dimethyl-tetrahydro-pyrimidin-4-one 
• 143956-10-9 (2S,5R)-1-Benzoyl-2-tert-butyl-3,5-dimethyl-tetrahydro-pyrimidin-4-one 
• 139119-52-1 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one 
• 143870-67-1 1-benzoyl-2(S)-tert-butyl-3-methyl-2,3-dihydro-4(1H)-pyrimidin-4-one 

Relevant academic research and scientific papers

An electrochemical interpretation of the mechanism of the chemical decarboxylation of 6-carboxyperhydropyrimidin-4-ones

The present work analyzes the anodic oxidation of the tetrabutylammonium salt of 1-benzoyl-2(S)-tert-butyl-6(S)-carboxyperhydropyrimidin-4-one, which is a useful starting material in the synthesis of enantiopure α-substituted β-amino acids. It was demonstrated that in CH2Cl2 solvent, the anodic oxidation reaction results in fast and complete decarboxylation, followed by proton elimination thereby leading to the same product of chemical (diacetoxyiodobenzene) oxidative decarboxylation. The electrochemical mechanism involves two electron transfer steps, but appears as a monoelectronic process owing to the release of one proton from the key acyliminium carbocation intermediate. The relative stability of this intermediate and the suppression of any solvolysis reaction in CH 2Cl2 allow for the detection of the acyliminium intermediate by means of cyclic voltammetry experiments. By contrast, in the presence of a nucleophilic solvent such as acetonitrile, the acyliminium intermediate is trapped in a typical Ritter reaction.

Synthesis of 2-substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and their derivatization utilizing the sonogashira coupling reaction in the enantioselective synthesis of α-substituted β-amino acids

(Chemical Equation Presented) A convenient, one-pot procedure for the synthesis of 1-benzoyl-2(S)-substituted-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-ones by tandem decarboxylation/β-iodination of the corresponding 6-carboxy-perhydropyrimidin-4-ones was devel

Enantioselective synthesis of β-amino acids. 7. Preparation of enantiopure α-substituted β-amino acids from 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one

Inexpensive natural α-amino acid L-asparagine was efficiently converted to either (R)- or (S)-α-alkylated β-amino acids in enantiomerically pure state. The key intermediate in this protocol is the enantiopure N,N-acetal pyrimidinone (S)-1, a masked chiral derivative of β-alanine.

Preparation and Assignment of Configuration of 1-Benzoyl-(2S)-tert-butyl-3-methyl-perhydropyrimidin-4-one. Useful Starting Material for the Enantioselective Synthesis of α-Substituted β-Amino Acids

(S)-Asparagine, an inexpensive β-amino acid was converted into the title heterocycle (+)-1 in very good overall yield.The highly selective trans methylation of (+)-1-Li, and the hydrolysis of the resulting adduct afforded (R)-α-methyl-β-alanine, allowing the assignment of the (S) configuration in (+)-1.