Potassium Carbonate → 2-[3-(6-Amino-2-butoxy-8-methoxy-9H-purin-9-yl)propyl]-1H-isoindole-1,3(2H)-dione
Reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:15][CH3:16])[NH:12]2)=[C:8]([NH2:17])[N:7]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH2:27][N:28]1[C:36](=[O:37])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]1=[O:38]>CN(C=O)C>[NH2:17][C:8]1[N:7]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[N:10]=[C:11]([O:15][CH3:16])[N:12]2[CH2:25][CH2:26][CH2:27][N:28]1[C:36](=[O:37])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]1=[O:38]Participants
5
Procedure
2-(Butyloxy)-8-(methyloxy)-9H-purin-6-amine (7.5 g, 31.6 mmol) was dissolved in DMF (100 ml) and potassium carbonate (4.37 g, 31.6 mmol) was added. After the suspension had been stirred at room temperature for 15 min., 2-(3-bromopropyl)-1H-isoindole-1,3(2H)-dione (8.00 g, 29.8 mmol) was added and the suspension was vigorously stirred at room temperature for 10 hours. The reaction mixture was extracted with ethyl acetate, washed with water, brine and dried. The crude material was recrystallized from EtOAc/diethyl ether to give the title compound in three different batches (2.02 g), (2.44 g) and (1.60 g).
Workup
- stirringthe suspension was vigorously stirred at room temperature for 10 hours
- extractionThe reaction mixture was extracted with ethyl acetate
- washwashed with water, brine
- customdried
- customThe crude material was recrystallized from EtOAc/diethyl ether
Sources & evidence
- ORD record
- ord-240774e8b74b41eb92c52cb122528333
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575181B2
Reaction notes
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