HCID 136013917, compound → HCID 136121403, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[C:3]=1[C:9]1[N:18]=[C:17]([N:19]2[CH2:23][CH2:22][C@@H:21]([NH:24]C(=O)OCC3C=CC=CC=3)[CH2:20]2)[C:16]2[C:11](=[CH:12][C:13]([CH3:35])=[CH:14][CH:15]=2)[N:10]=1>CO.[Pd]>[NH2:24][C@@H:21]1[CH2:22][CH2:23][N:19]([C:17]2[C:16]3[C:11](=[CH:12][C:13]([CH3:35])=[CH:14][CH:15]=3)[N:10]=[C:9]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[OH:8])[N:18]=2)[CH2:20]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Under an N2 atmosphere, Pd/C (10% weight, 210 mg) was added to a solution of (R)-benzyl 1-(2-(2-fluoro-6-hydroxyphenyl)-7-methylquinazolin-4-yl)pyrrolidin-3-ylcarbamate (2.1 g, 4.44 mmol) in MeOH (60 mL). After purging 2 times with N2 and evacuating the atmosphere in the flask containing the reaction mixture, the reaction was stirred under an H2 atmosphere for 16 h. Since the reaction was not complete, an additional 200 mg Pd/C was added, and the reaction was stirred for an additional 4 h. The mixture was filtered through a pad of Celite (150 mL) using 1.8 mL MeOH, and the filtrate was concentrated under reduced pressure to obtain (R)-2-(4-(3-aminopyrrolidin-1-yl)-7-methylquinazolin-2-yl)-3-fluorophenol as a yellow solid (1.4 g, 93%). LC/MS: m/z 339.1 (M+H)+ at 1.05 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).