143870-66-0

Basic information

• Product Name: 4(1H)-Pyrimidinone, 1-benzoyl-2-(1,1-dimethylethyl)-2,3-dihydro-, (S)-
• CAS NO: 143870-66-0
• Molecular Formula: C15H18N2O2
• Molecular Weight: 258.32
• Mol File: 143870-66-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 4(1H)-Pyrimidinone, 1-benzoyl-2-(1,1-dimethylethyl)-2,3-dihydro-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4(1H)-Pyrimidinone, 1-benzoyl-2-(1,1-dimethylethyl)-2,3-dihydro-, (S)-(143870-66-0)
• EPA Substance Registry System: 4(1H)-Pyrimidinone, 1-benzoyl-2-(1,1-dimethylethyl)-2,3-dihydro-, (S)-(143870-66-0)

Safety Data

• Hazardous Substances Data: 143870-66-0(Hazardous Substances Data)

Upstream product

• 630-19-3 pivalaldehyde 
• 131791-76-9 cis-2-tert-butyl-6(S)-potassium carboxylate-perhydropyrimidin-4-one 
• 98-88-4 benzoyl chloride 
• 747376-89-2 C₉H₁₆N₂O₃ 
• 143870-65-9 1-benzoyl-2(S)-tert-butyl-6(S)-carboxy-perhydropyrimidin-4-one 
• 762-72-1 allyl-trimethyl-silane 

Downstream Products

• 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 
• 143870-67-1 1-benzoyl-2(S)-tert-butyl-3-methyl-2,3-dihydro-4(1H)-pyrimidin-4-one 

Relevant articles and documents

Tandem reactions initiated by the oxidative decarboxylation of 1-benzoyl-2(S)-tert-butyl-6(S)-carboxyperhydropyrimidin-4-one

Treatment of the title perhydropyrimidinone with diacetoxyiodobenzene and iodine followed by addition of allyltrimethylsilane and boron trifluoride etherate afforded 1-benzoyl-2(S)-tert-butyl-2,3-dihydro-4(H)-pyrimidin-4-one in 65-71% yield, via an efficient three-step radical decarboxylation-oxidation-β-elimination tandem reaction. In contrast, when addition of allyltrimethylsilane/BF3·OEt2 was suppressed, a remarkable five-step tandem process led to the formation of vinylic iodide, 1-benzoyl-2(S)-tert-butyl-5-iodo-2,3-dihydro-4(H)-pyrimidin-4-one as the main product.

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.

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.