HCID 54692278, compound → HCID 54692421, compound
Reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[CH2:22][CH:21]([CH2:23][CH2:24][N:25](OC)[CH3:26])[N:10]3[C:11](=[O:20])[N:12]([CH:17]([CH3:19])[CH3:18])[C:13](=[O:16])[C:14]([OH:15])=[C:9]3[C:8]2=[O:29])=[CH:4][CH:3]=1>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH2:22][CH:21]([CH2:23][CH2:24][NH:25][CH3:26])[N:10]3[C:11](=[O:20])[N:12]([CH:17]([CH3:19])[CH3:18])[C:13](=[O:16])[C:14]([OH:15])=[C:9]3[C:8]2=[O:29])=[CH:30][CH:31]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(4-Fluorobenzyl)-9-hydroxy-7-isopropyl-4-{2-[methoxy(methyl)amino]ethyl}-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,6,8(7H)-trione (108 mg, 0.20 mmol, from Example 6) was dissolved in degassed MeOH (8 mL). The solution was degassed and purged three times with nitrogen and then treated with 10% palladium on activated carbon (25 mg) and 6 N aqueous HCl solution (10 drops). The mixture was degassed and purged with nitrogen three times more and placed under hydrogen atmosphere for 24 h. The reaction was filtered through Celite, washing with MeOH, and the filtrate was concentrated in vacuo to a dark yellow oil. Purification by reverse phase chromatography [95:5 water (+0.1% TFA)/MeCN (+0.1% TFA) to 5:95 water (+0.1% TFA)/MeCN (+0.1% TFA)] afforded the title compound as a gray foam. 1H NMR (500 MHz, CD3OD) δ 7.45-7.43 (m, 2H), 7.16-7.12 (m, 2H), 5.19 (dt, J=7.0, 14.0 Hz, 1H), 4.94 (d, J=14.5 Hz, 1H), 4.85-4.84 (m, 1H), 4.50 (d, J=14.5 Hz, 1H), 3.84 (dd, J=4.0, 14.0 Hz, 1H), 3.43 (dd, J=1.5, 14.0 Hz, 1H), 2.92-2.78 (m, 2H), 2.64 (s, 3H), 1.96-1.88 (m, 1H), 1.77-1.70 (m, 1H), 1.47 (dd, J=4.5, 6.5 Hz, 6H). HRMS (FT/ES) M+H: calcd for (C20H26FN4O4)+ 405.1933. found 405.1945.