Sodium Methoxide → HCID 57699783, compound

HRID 1010958Notes

Reaction equation

HRID 1010958 reaction equation
Br[C:2]1[N:3]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[N:5]=2.[CH3:24][O-:25].[Na+]>CCOC(C)=O>[CH3:16][CH:15]([CH3:17])[CH2:14][CH2:13][O:12][C:6]1[N:5]=[C:4]2[C:9]([N:10]=[C:2]([O:25][CH3:24])[N:3]2[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)=[C:8]([NH2:11])[N:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 576996758-Bromo-2-[(3-methylbutyl)oxy]-9-(tetrahydro-2H-Pyran-2-yl)-9H-Purin-6-amine

Product 1

HCID 57699783HCID 57699783, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-bromo-2-[(3-methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (314 mg) was added sodium methoxide solution (0.460 mL, 30% wt. MeOH) and the mixture was stirred at reflux for 4 h. The reaction was allowed to cool and was concentrated in vacuo to give an orange residue. The residue was taken up in EtOAc (20 mL) and was extracted with saturated ammonium chloride solution (20 mL), followed by water (20 mL). The organics were separated, dried over MgSO4, filtered and concentrated in vacuo to give the title compound as a light orange solid (210 mg).

Workup

  1. temperatureat reflux for 4 h
  2. temperatureto cool
  3. concentrationwas concentrated in vacuo
  4. customto give an orange residue
  5. extractionwas extracted with saturated ammonium chloride solution (20 mL)
  6. customThe organics were separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-010b1a3da70b47dcbc620ff88b2302d7
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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