Sodium Methoxide → 2-[(1-Methylbutyl)oxy]-8-methoxy-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][CH:13]([CH3:17])[CH2:14][CH2:15][CH3:16])[N:5]=2.[CH3:24][O-:25].[Na+]>CO.[Cl-].[NH4+]>[CH3:17][CH: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
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 8-bromo-2-[(1-methylbutyl)oxy]-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (493 mg) in dry MeOH (4.37 mL) was added sodium methoxide solution (0.722 mL, 30% wt. in MeOH) and the mixture was stirred at reflux for 6 h. A further portion of sodium methoxide solution (0.120 mL, 30% wt. in MeOH) was added and the reaction was continued for 90 mins. The reaction was cooled and concentrated in vacuo to give an orange residue. The residue was taken up in saturated ammonium chloride (25 mL) and washed with EtOAc (25 mL). The organics were separated and washed with water (15 mL). The organics were separated, dried over MgSO4, filtered and concentrated in vacuo to give the title compound as an orange foam (313 mg).
Workup
- temperatureat reflux for 6 h
- temperatureThe reaction was cooled
- concentrationconcentrated in vacuo
- customto give an orange residue
- washwashed with EtOAc (25 mL)
- customThe organics were separated
- washwashed with water (15 mL)
- customThe organics were separated
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-da062ce110fa4ef887e7a59ff1d70f2b
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977344B2
Reaction notes
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