Methanol → Methyl 2-(4-ethyl-6-oxo-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoate
Reaction equation
S(Cl)(Cl)=O.[CH2:5]([C:7]1[N:8]=[C:9]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[NH:10][C:11](=[O:20])[C:12]=1[CH:13]([CH2:17][CH2:18][CH3:19])[C:14]([OH:16])=[O:15])[CH3:6].[CH3:27]O>>[CH2:5]([C:7]1[N:8]=[C:9]([N:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[NH:10][C:11](=[O:20])[C:12]=1[CH:13]([CH2:17][CH2:18][CH3:19])[C:14]([O:16][CH3:27])=[O:15])[CH3:6]Participants
4
Procedure
To a solution cold solution of methanol (40 mL) was added thionyl chloride (5.8 mL; 80 mmol) dropwise. The acidic solution was added to a flask containing 2-(4-ethyl-6-oxo-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoic acid (2.416 g; 7.86 mmol) and the mixture was heated to reflux for 18 h. The reaction mixture was concentrated under reduced pressure and the product was used as such in the next reaction.