Potassium Carbonate → HCID 57699654, compound

HRID 1010965Notes

Reaction equation

HRID 1010965 reaction equation
[CH3:1][CH:2]([CH2:17][CH3:18])[CH2:3][O:4][C:5]1[N:13]=[C:12]2[C:8]([N:9]=[C:10]([O:14][CH3:15])[NH:11]2)=[C:7]([NH2:16])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>CN(C=O)C.CCOC(C)=O>[CH3:1][CH:2]([CH2:17][CH3:18])[CH2:3][O:4][C:5]1[N:13]=[C:12]2[C:8]([N:9]=[C:10]([O:14][CH3:15])[N:11]2[CH2:26][CH:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[C:7]([NH2:16])[N:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27732864-(Bromomethyl)oxaneHCID 178447006HCID 178447006, compound

Product 1

HCID 57699654HCID 57699654, compoundYield 35.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-[(2-methylbutyl)oxy]-8-methoxy-9H-purin-6-amine (109 mg) in dry DMF (1.86 mL) was added potassium carbonate (165 mg) and the mixture was stirred at 60° C. for 90 mins. The mixture was cooled to room temperature and 4-(bromomethyl)tetrahydro-2H-pyran (59 mg) was added. The reaction was stirred at 50° C. overnight and was cooled to room temperature. The mixture was taken up in EtOAc (15 mL) and washed with water (2×10 mL). The organics were separated, dried over MgSO4, filtered and concentrated in vacuo to give a yellow viscous oil. The material was purified by C18 reverse phase chromatography (ISCO) using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluent (20-60%) to afford the title compound as a yellow oil (41 mg).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringThe reaction was stirred at 50° C. overnight
  3. temperaturewas cooled to room temperature
  4. washwashed with water (2×10 mL)
  5. customThe organics were separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a yellow viscous oil
  10. customThe material was purified by C18 reverse phase chromatography (ISCO)

Sources & evidence

ORD record
ord-c957dabca68d42519f00edad7f395287
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…