benzyl((S)-1-(6-fluoro-2-(2-hydroxyphenyl)quinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate → 2-(4-((S)-3-(aminomethyl)pyrrolidin-1-yl)-6-fluoroquinazolin-2-yl)phenol
Reaction equation
C(OC(=O)[NH:10][CH2:11][C@@H:12]1[CH2:16][CH2:15][N:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([F:27])[CH:25]=3)[N:20]=[C:19]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[OH:34])[N:18]=2)[CH2:13]1)C1C=CC=CC=1>[Pd].CO>[NH2:10][CH2:11][C@@H:12]1[CH2:16][CH2:15][N:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([F:27])[CH:25]=3)[N:20]=[C:19]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[OH:34])[N:18]=2)[CH2:13]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Under an N2 atmosphere, a mixture of benzyl((S)-1-(6-fluoro-2-(2-hydroxyphenyl)quinazolin-4-yl)pyrrolidin-3-yl)methylcarbamate (0.770 g, 1.6 mmol) and MeOH (5 mL) was added to Pd/C (77 mg, 10% weight Pd on carbon) weighed into a 100 mL flask. After the atmosphere in the flask was evacuated and purged with N2 three times, the reaction mixture was vigorously stirred under an H2 atmosphere at ambient pressure overnight and then filtered through a pad of Celite, concentrated, and dried to obtain 2-(4-((S)-3-(aminomethyl)pyrrolidin-1-yl)-6-fluoroquinazolin-2-yl)phenol (0.45 g, 81%). LC/MS: m/z 459.5 (M+H)+ at 2.81 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).
Workup
- customweighed into a 100 mL flask
- customAfter the atmosphere in the flask was evacuated
- custompurged with N2 three times
- filtrationfiltered through a pad of Celite
- concentrationconcentrated
- customdried
Sources & evidence
- ORD record
- ord-06d7477857224112bbeb9269ebf41e74
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08283354B2
Reaction notes
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