4-[6-(2-Ethoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester → Piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide
Reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:31])[NH:15][C:16]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH2:29][CH3:30])[N:19]=[CH:18][N:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C>ClCCl.C(O)(C(F)(F)F)=O>[CH2:29]([O:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:20]1[N:19]=[CH:18][N:17]=[C:16]([NH:15][C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:31])[CH:21]=1)[CH3:30]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred solution of 4-[6-(2-ethoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid tert-butyl ester (IV), (0.500 g, 1.17 mmol) in dry dichloromethane (1.5 ml), TFA (1.5 ml) was added at 0° C. and the reaction mixture was stirred for 2-3 hours. After completion of the reaction (monitored by TLC) the solvent mixture was removed under reduced pressure and dichloromethane was added to the residue. Solid sodium carbonate was added and the mixture was stirred for 3-4 hours. Then it was filtered and washed with dichloromethane. The combined filtrate was concentrated under reduced pressure to obtain a solid which was washed with 10% ethyl acetate/hexane to remove nonpolar impurities, giving piperidine-4-carboxylic acid [6-(2-ethoxy-phenyl)-pyrimidin-4-yl]-amide (compound #1A) as pure white solid (0.19 g, 50%).