Sodium Methoxide → HCID 57699821, compound

HRID 1010963Notes

Reaction equation

HRID 1010963 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][CH:14]([CH3:17])[CH2:15][CH3:16])[N:5]=2.[CH3:24][O-:25].[Na+]>CO>[CH3:17][CH:14]([CH2:15][CH3:16])[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 57699761HCID 57699761, compound

Product 1

HCID 57699821HCID 57699821, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8-bromo-2-[(2-methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (284 mg) in dry MeOH (2.54 mL) was added sodium methoxide solution (0.416 mL, 30% wt. MeOH) and the mixture was stirred at reflux for 1 h. The reaction was allowed to cool and was concentrated in vacuo. The resulting residue was dissolved in EtOAc (15 mL) and was poured into saturated ammonium chloride solution (15 mL). The organics were separated, dried over MgSO4, filtered and concentrated in vacuo to give the title compound as an orange foam (199 mg).

Workup

  1. temperatureat reflux for 1 h
  2. temperatureto cool
  3. concentrationwas concentrated in vacuo
  4. dissolutionThe resulting residue was dissolved in EtOAc (15 mL)
  5. additionwas poured into saturated ammonium chloride solution (15 mL)
  6. customThe organics were separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ba498ddbb734dfdb394e55bc263b1ac
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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