Sodium Methoxide → 8-(Methyloxy)-2-{[(1S)-1-methylpropyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine
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]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- temperaturethe mixture heated
- temperatureto reflux for 2.5 hours
- waitThe reaction mixture was left
- concentrationconcentrated in vacuo
- customthe residue partitioned between dichloromethane (40 ml) and saturated ammonium chloride solution (40 ml)
- customThe layers were separated
- extractionthe aqueous phase was re-extracted with dichloromethane (40 ml)
- concentrationThe combined organic extracts were concentrated in vacuo
Sources & evidence
- ORD record
- ord-18e738ba29184c58b63fbca9df0208ab
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067426B2
Reaction notes
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