Methanol → 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)[C@H:30]([OH:34])[C@@H:29]3[OH:35])[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.[CH3:36][OH:37]>[Pd]>[OH:35][C@H:29]1[C@@H:30]([OH:34])[C@H:31]([O:37][CH3:36])[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[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)[N:26]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(1S,2S,3S,4R)-(2,3,4-trihydroxycyclopentan-1-yl)oxy]quinazoline [cf. Example 33(4)] (1.00 g) in methanol (15 ml) is added 10% palladium/carbon (200 mg), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature for 3 hours. The reaction mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure, and the residue is dissolved in ethanol (35 ml) and thereto is added fumaric acid (242 mg). The precipitated crystals are dissolved by adding water to the mixture. The mixture is filtered and the filtrate is evaporated to dryness under reduced pressure, and the resulting residue is recrystallized from water-ethanol to give 4-[(1S,2S,3S,4R)-(2,3,4-trihydroxycyclopentan-1-yl)oxy]-2-(1-piperazinyl)quinazoline 1/2 fumarate (390 mg) as crystals.