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

HRID 527773Notes

Reaction equation

HRID 527773 reaction equation
F[C:2](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+].BrC[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][Cl:38]>CN(C=O)C.O>[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[CH2:33][CH2:34][CH2:35][CH2:36][CH:37]([Cl:38])[CH3:2])=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 805161-Bromo-6-chlorohexaneHCID 178450370HCID 178450370, compound

Product 1

HCID 667270732-(Butyloxy)-9-(5-chlorohexyl)-8-(methyloxy)-9H-purin-6-amineYield 115.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(butyloxy)-8-(methyloxy)-9H-purin-6-amine trifluoroacetate salt (3 g, 8.54 mmol) in DMF (30 ml) was added potassium carbonate (2.95 g, 21.35 mmol) and the mixture stirred at 60° C. for 1 hour under an atmosphere of nitrogen. The mixture was then cooled to room temperature and 1-bromo-6-chlorohexane (1.27 ml, 8.54 mmol) was added and the reaction heated to 50° C. and stirred overnight under an atmosphere of nitrogen. The reaction mixture was diluted with water (ca. 50 ml) and extracted with ethyl acetate (2×70 ml). The combined organic extracts were dried (MgSO4), filtered and the filtrate concentrated to give an orange oil (ca. 3.5 g). This material was dissolved in dichloromethane and purified on a Flashmaster II (70 g aminopropyl cartridge) using a 0-100% ethyl acetate in cyclohexane gradient over 60 mins. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a yellow oil which solidified to a pale yellow solid (1.2 g).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. temperaturethe reaction heated to 50° C.
  3. stirringstirred overnight under an atmosphere of nitrogen
  4. extractionextracted with ethyl acetate (2×70 ml)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-6c0781b57ab74d03a49c10bac5c6d0b6
Source dataset
uspto-grants-2016_05
Patent number
US09346806B2

Reaction notes

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