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

HRID 590427Notes

Reaction equation

HRID 590427 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:18](=O)([O-])[O-].[K+].[K+].BrC[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][Cl:31]>CN(C=O)C.O>[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:15][CH3:16])[N:12]2[CH2:26][CH2:27][CH2:28][CH2:29][CH:30]([Cl:31])[CH3:18])=[C:8]([NH2:17])[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 805161-Bromo-6-chlorohexaneHCID 574571342-(Butyloxy)-8-(methyloxy)-9H-purin-6-amine

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 trifuoroacetate 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). LCMS (System D): tRET=3.59 min; MH+=356, 358

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-faf55a94591245c1be82932f6b55baf9
Source dataset
uspto-grants-2016_01
Patent number
US09233962B2

Reaction notes

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