143870-67-1

Basic information

• Product Name: 4(1H)-Pyrimidinone, 1-benzoyl-2-(1,1-dimethylethyl)-2,3-dihydro-3-methyl-, (S)-
• CAS NO: 143870-67-1
• Molecular Formula: C16H20N2O2
• Molecular Weight: 272.347
• Mol File: 143870-67-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4(1H)-Pyrimidinone, 1-benzoyl-2-(1,1-dimethylethyl)-2,3-dihydro-3-methyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4(1H)-Pyrimidinone, 1-benzoyl-2-(1,1-dimethylethyl)-2,3-dihydro-3-methyl-, (S)-(143870-67-1)
• EPA Substance Registry System: 4(1H)-Pyrimidinone, 1-benzoyl-2-(1,1-dimethylethyl)-2,3-dihydro-3-methyl-, (S)-(143870-67-1)

Safety Data

• Hazardous Substances Data: 143870-67-1(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 131791-76-9 cis-2-tert-butyl-6(S)-potassium carboxylate-perhydropyrimidin-4-one 
• 630-19-3 pivalaldehyde 
• 143870-65-9 1-benzoyl-2(S)-tert-butyl-6(S)-carboxy-perhydropyrimidin-4-one 
• 143870-66-0 1-benzoyl-2(S)-tert-butyl-2,3-dihydro-4(1H)-pyrimidin-4-one 
• 74-88-4 methyl iodide 

Downstream Products

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

Relevant articles and documents

Alternative procedure for the synthesis of enantiopure 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one, a useful starting material for the enantioselective synthesis of α-substituted β-amino acids

The title heterocycle is prepared in enantiomerically pure form and in 46-50% overall yield from (S)-asparagine, a readily available starting material. The synthetic route described in this report represents a major improvement over the original procedure (Tetrahedron: Asymmetry 1991, 3, 723), that afforded a 24-32% overall yield. Furthermore, the use of toxic reagents such as Pb(OAc)4 and dimethyl sulfate is avoided in the present protocol.

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.