Potassium Carbonate → 3-(1-(6-Amino-9H-purin-9-yl)ethyl)-4-(3-(dimethylamino)phenyl)-1H-isochromen-1-one
Reaction equation
Br[CH:2]([C:4]1[O:5][C:6](=[O:23])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N:20]([CH3:22])[CH3:21])[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3].[N:24]1[C:32]([NH2:33])=[C:31]2[C:27]([NH:28][CH:29]=[N:30]2)=[N:26][CH:25]=1.C([O-])([O-])=O.[K+].[K+]>>[NH2:33][C:32]1[N:24]=[CH:25][N:26]=[C:27]2[C:31]=1[N:30]=[CH:29][N:28]2[CH:2]([C:4]1[O:5][C:6](=[O:23])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N:20]([CH3:22])[CH3:21])[CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3]Participants
4
Procedure
The title compound was made in a similar way as that of the compound of example 1, using 3-(1-bromoethyl)-4-(3-(dimethylamino)phenyl)-1H-isochromen-1-one (intermediate C8, 86 mg, 0.231 mmol), 9H-purin-6-amine (46.8 mg, 0.347 mmol) and K2CO3 (47.9 mg, 0.347 mmol) to give the title compound (36 mg, 37%). The resulting mixture was straightforward purified via reverse phase chromatography with a Biotage C18 SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%). The resulting product was further purified by Preparative HPLC (method 1) to give the title compound (12 mg, 12%).
Sources & evidence
- ORD record
- ord-5b59f75add2048119598877d987c37de
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321776B2
Reaction notes
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