Selective N-alkylation of 4(3H)-pyrimidone derivatives for the preparation of pharmaceutically important compounds

ORGN 751

Sun Hwa Lee, sugarbabi@naver.com1, Hakwon Kim, hwkim@khu.ac.kr2, Ji Han Kim3, and Joon Kwang Lee3. (1) Department of Chemistry, Kyunghee university, Seocheon-dong, Giheung-gu, Yongin-si, Gyeonggi-do, 446-701, South Korea, (2) Department of Chemistry and The Institute of Natural Science, Kyung Hee University, Seocheon-dong, Giheung-gu, Yongin-si, Gyeonggi-do, 446-701, South Korea, (3) Boryung pharmacetical co. ltd
Recently 4(3H)-pyrimidone derivatives, especially 3-N-alkylated ones, have been considered as one of the pharmaceutically important drugs, such as ACE inhibitor and inhibitor of HIV intergrase etc. However, there still is a need for efficient methods allowing the selective N-alkylation of 4(3H)-pyrimidones over O-alkylation. We have investigated the N- and O-alkylation of this pyrimidone system under various conditions (base, solvent, temperature etc) and then developed the selective N-alkylation method to be applied for the preparation of ACE inhibitor containing a 3(N)-alkylated-4-pyrimidone nucleus.