245679-95-2

Upstream product

• 245679-90-7 (2S)-1,3-dibenzyl-1,2,3,4,5,6-hexahydro-5-{[2-(methoxymethyl)pyrrolidin-1-yl]imino}pyrimidine-2-one 
• 100-46-9 benzylamine 
• 65838-17-7 1,3-di-(N-benzylamino)-2-hydroxypropane 
• 245679-89-4 1,3-dibenzyl-1,2,3,4,5,6-hexahydropyrimidine-2,5-dione 
• 245679-88-3 1,3-dibenzyl-1,2,3,4,5,6-hexahydro-5-hydroxypyrimidin-2-one 

Relevant academic research and scientific papers

A highly flexible route to 1,2,3,4,5,6-hexahydro-5-hydroxypyrimidin-2-ones as potential HIV protease inhibitors

The first asymmetric synthesis of potential HIV protease inhibitors of type II, III and IV is described. Key step of the synthesis is an auxiliary based stereoselective alkylation by means of the (R)-1-amino-2-methoxymethylpyrrolidine (RAMP)- / (S)-1-amino-2-methoxymethylpyrrolidine (SAMP)-hydrazone method starting from a readily available key building block, pyrimidin-2,5-dione (6). The synthesis is short and highly versatile in the choice of the substitution pattern as well as the absolute configuration of the alkylated 1,2,3,4,5,6-Hexahydro-5-hydroxypyrimidin-2-ones.

Asymmetric synthesis of 1,2,3,4,5,6-hexahydro-5-hydroxypyrimidin-2-ones as potential HIV-protease inhibitors

The first asymmetric synthesis of potential cyclic urea HIV protease inhibitors of Type 2 is reported. The synthesis is short and highly versatile in the choice of the substitution pattern and absolute configuration of the products starting from readily available materials. Nonchiral central building block 5 was synthesized and subsequently asymmetrically alkylated under (R)-/(S)-1-amino-2-(methoxymethyl)pyrrolidine (RAMP/SAMP)-auxiliary control to provide 8a-e. The alkylated ketones then were reduced to the target compounds 9a-e, with good-to-excellent overall yields, as well as diastereoisomeric and enantiomeric purities.