Sodium Methoxide → 2-{[(1R)-1-Methylbutyl]oxy}-8-(methyloxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine
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][C@H:13]([CH3:17])[CH2:14][CH2:15][CH3:16])[N:5]=2.[CH3:24][O-:25].[Na+]>CO>[CH3:17][C@@H: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)[CH2:14][CH2:15][CH3:16]Participants
4
Procedure
8-bromo-2-{[(1R)-1-methylbutyl]oxy}-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (5.23 g, 13.61 mmol) was heated to reflux with 25% sodium methoxide in methanol (8.8 ml, 13.61 mmol) and methanol (40 ml) for 4 hours. The reaction mixture was concentrated under reduced pressure and partitioned between saturated ammonium chloride (100 ml) and dichloromethane (100 ml). The aqueous was washed with further dichloromethane (100 ml) and the combined organics passed through a hydrophobic frit and concentrated to give the title compound as a pale yellow foam (4.80 g).