Sodium Methoxide → 2-[(2,2-Dimethylpentyl)oxy]-8-methoxy-9-(tetrahydro-2H-pyran-2-yl)-9H-Purin-6-amine

HRID 1010948Notes

Reaction equation

HRID 1010948 reaction equation
Br[C:2]1[N:3]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][CH2:13][C:14]([CH3:19])([CH3:18])[CH2:15][CH2:16][CH3:17])[N:5]=2.[CH3:26][O-:27].[Na+]>CO.[Cl-].[NH4+]>[CH3:18][C:14]([CH3:19])([CH2:15][CH2:16][CH3:17])[CH2:13][O:12][C:6]1[N:5]=[C:4]2[C:9]([N:10]=[C:2]([O:27][CH3:26])[N:3]2[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[C:8]([NH2:11])[N:7]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 576997978-Bromo-2-[(2,2-dimethylpentyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 576996322-[(2,2-Dimethylpentyl)oxy]-8-methoxy-9-(tetrahydro-2H-pyran-2-yl)-9H-Purin-6-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 8-bromo-2-[(2,2-dimethylpentyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (475 mg) in dry MeOH (3.92 mL) was added sodium methoxide solution (0.649 mL, 30% wt. in MeOH). The reaction mixture was stirred at reflux for 5 h. The reaction was cooled and concentrated in vacuo to give an orange residue. The residue was taken up in saturated ammonium chloride solution (25 mL) and was extracted with EtOAc (25 mL). The organic layer was separated and washed with water (15 mL). The organics were separated, dried over MgSO4, filtered and concentrated in vacuo to give the title compound as an orange solid (323 mg).

Workup

  1. temperatureat reflux for 5 h
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated in vacuo
  4. customto give an orange residue
  5. extractionwas extracted with EtOAc (25 mL)
  6. customThe organic layer was separated
  7. washwashed with water (15 mL)
  8. customThe organics were separated
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62bc22b463404924b496d5dfea99449c
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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