HCID 67581949, compound → HCID 57098847, compound
Reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][C@H:28]3[CH2:32][C@@H:31]([O:33][CH3:34])[C@H:30]([OH:35])[C@@H:29]3[OH:36])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[OH:36][C@H:29]1[C@@H:30]([OH:35])[C@H:31]([O:33][CH3:34])[CH2:32][C@@H:28]1[O:27][C:25]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([N:14]2[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]2)[N:26]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(1S,2S,3R,4R)-(2,3-dihydroxy-4-methoxycyclopentan-1-yl)oxy]quinazoline (600 mg) in methanol (12 ml) is added 10% palladium/carbon (120 mg), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature for 20 hours. The reaction mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure to give 4-[(1S,2S,3R,4R)-(2,3-dihydroxy-4-methoxycyclopentan-1-yl)oxy]-2-(1-piperazinyl)quinazoline (415 mg) as foam.