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Potassium Carbonate → 2-(Butyloxy)-9-(5-chloropentyl)-8-(methyloxy)-9H-purin-6-amine

HRID 527772
Notes
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Reaction equation

HRID 527772 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][Cl:37]>CN(C=O)C>[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][Cl:37])=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 960701-Bromo-5-chloropentaneHCID 178450370HCID 178450370, compound

Product 1

HCID 592526362-(Butyloxy)-9-(5-chloropentyl)-8-(methyloxy)-9H-purin-6-amineYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-(Butyloxy)-8-(methyloxy)-9H-purin-6-amine trifluoroacetate (2 g, 5.69 mmol) and potassium carbonate (1.967 g, 14.23 mmol) were suspended in DMF (20 ml) and heated to 50° C., under nitrogen for 1 hour. The mixture was cooled to room temperature, 1-bromo-5-chloropentane (0.75 ml, 5.69 mmol) was added and stirring was continued at room temperature for 18 hours. The reaction mixture was partitioned between DCM (40 ml) and water (40 ml) and the layers were separated using a hydrophobic frit. The aqueous layer was extracted again with DCM (10 ml) and the combined organics were washed with saturated lithium chloride solution, separated (hydrophobic frit) and concentrated in vacuo to give the title compound as a yellow oil (1.946 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe reaction mixture was partitioned between DCM (40 ml) and water (40 ml)
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted again with DCM (10 ml)
  5. washthe combined organics were washed with saturated lithium chloride solution
  6. customseparated (hydrophobic frit)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a820ba3c16f84804b39f52a7f0bee4a2
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09346806B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes