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Potassium Carbonate → 2-[3-(6-Amino-2-butoxy-8-methoxy-9H-purin-9-yl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 2036347
Notes
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Reaction equation

HRID 2036347 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 574571342-(Butyloxy)-8-(methyloxy)-9H-purin-6-amine

Product 1

HCID 582909572-[3-(6-Amino-2-butoxy-8-methoxy-9H-purin-9-yl)propyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. stirringthe suspension was vigorously stirred at room temperature for 10 hours
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washwashed with water, brine
  4. customdried
  5. customThe crude material was recrystallized from EtOAc/diethyl ether

Sources & evidence

ORD record
ord-240774e8b74b41eb92c52cb122528333
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08575181B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes