Sodium Methoxide → 8-(Methyloxy)-2-{[(1S)-1-methylpropyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

HRID 590453Notes

Reaction equation

HRID 590453 reaction equation
Br[C:2]1[N:3]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][C@@H:13]([CH3:16])[CH2:14][CH3:15])[N:5]=2.[CH3:23][O-:24].[Na+]>CO>[CH3:23][O:24][C:2]1[N:3]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][C@@H:13]([CH3:16])[CH2:14][CH3:15])[N:5]=2

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 592525528-Bromo-2-{[(1S)-1-methylpropyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Product 1

HCID 592526388-(Methyloxy)-2-{[(1S)-1-methylpropyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

8-Bromo-2-{[(1S)-1-methylpropyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.79 g, 4.83 mmol) was dissolved in methanol (15 ml) and 25% sodium methoxide in methanol (3.2 ml, 4.83 mmol) was added and the mixture heated to reflux for 2.5 hours. The reaction mixture was left standing at room temperature overnight and then concentrated in vacuo and the residue partitioned between dichloromethane (40 ml) and saturated ammonium chloride solution (40 ml). The layers were separated using a hydrophobic frit and the aqueous phase was re-extracted with dichloromethane (40 ml). The combined organic extracts were concentrated in vacuo to give the title compound as a yellow foam (1.65 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2.5 hours
  3. waitThe reaction mixture was left
  4. concentrationconcentrated in vacuo
  5. customthe residue partitioned between dichloromethane (40 ml) and saturated ammonium chloride solution (40 ml)
  6. customThe layers were separated
  7. extractionthe aqueous phase was re-extracted with dichloromethane (40 ml)
  8. concentrationThe combined organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-fede78141dab4bb0a1a3b603cdc955ef
Source dataset
uspto-grants-2016_01
Patent number
US09233962B2

Reaction notes

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