131791-76-9

Basic information

• Product Name: cis-2-tert-butyl-6(S)-potassium carboxylate-perhydropyrimidin-4-one
• CAS NO: 131791-76-9
• Molecular Weight: 238.328
• Mol File: 131791-76-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: cis-2-tert-butyl-6(S)-potassium carboxylate-perhydropyrimidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: cis-2-tert-butyl-6(S)-potassium carboxylate-perhydropyrimidin-4-one(131791-76-9)
• EPA Substance Registry System: cis-2-tert-butyl-6(S)-potassium carboxylate-perhydropyrimidin-4-one(131791-76-9)

Safety Data

• Hazardous Substances Data: 131791-76-9(Hazardous Substances Data)

Upstream product

• 70-47-3 L-asparagine 
• 630-19-3 pivalaldehyde 

Downstream Products

• 143870-65-9 1-benzoyl-2(S)-tert-butyl-6(S)-carboxy-perhydropyrimidin-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 
• 143870-66-0 1-benzoyl-2(S)-tert-butyl-2,3-dihydro-4(1H)-pyrimidin-4-one 
• 138723-44-1 (2S,6S)-2-tert-butyl-1-carbobenzoxy-6-carboxy-4-pyrimidone 

Relevant articles and documents

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.

Enantiomerically pure dihydropyrimidinones as reagents and auxiliaries for asymmetric synthesis

We report herein full experimental details of the synthesis, structure, and reactivity of (R)- and (S)-2-tert-butyl-l-carbomethoxy-2,3-dihydropyrimidin-4(lH)-one (1). The synthesis employs asparagine as the starting material and provides 1 in 55% yield without the need for Chromatographic purification. The structure of 1, as determined by X-ray crystallographic analysis, demonstrates significant pyramidalization at the C4 (carbonyl) and N1 centers, with little evidence of conjugation of Nl with the αβ,-unsaturated (vinylogous urea) system. In contrast, compound 11 [2-tert-butyl-3-((S)-O-methylmandeloyl)-2,3-dihydropyrimidin-4(lH)-one] shows strong coupling of Nl to the αβ,-unsaturated system, as evidenced by changes in bond lengths and torsional angles. Compound 1 has proven useful as a reagent for the synthesis of enantiomerically pure β-aryl-β-amino acids. The key step in this protocol is the palladium-catalyzed conjugate addition of aryl iodides to 1. Evidence is presented to support a mechanism for this reaction that involves an unprecedented transannular hydride transfer into the palladium coordination sphere. In additional experiments, 1 has been employed as an auxiliary for the synthesis of enantiomerically pure α-substituted carboxylic acids. The crystalline properties of 1 and many of its derivatives allow for simplified purification procedures to be utilized.