Potassium Carbonate → N2-butyl-8-(methoxy)-9-[4-(tetrahydro-2H-pyran-3-yl)butyl]-9H-purine-2,6-diamine
Reaction equation
[CH2:1]([NH:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:15][CH3:16])[NH:12]2)=[C:8]([NH2:17])[N:7]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:29][CH2:30][CH2:31][CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][O:35][CH2:34]1)(=O)=O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([NH:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:15][CH3:16])[N:12]2[CH2:29][CH2:30][CH2:31][CH2:32][CH:33]2[CH2:38][CH2:37][CH2:36][O:35][CH2:34]2)=[C:8]([NH2:17])[N:7]=1)[CH2:2][CH2:3][CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a solution of N2-butyl-8-(methoxy)-9H-purine-2,6-diamine (250 mg) in dry N,N-dimethylformamide (4.46 ml) at room temperature was added potassium carbonate (395 mg). The reaction mixture was stirred at 60° C. for 90 min. The reaction was cooled to room temperature and 4-(tetrahydro-2H-pyran-3-yl)butyl methanesulfonate (186 mg) was added and the reaction stirred at 90° C. for 2 hours. The reaction mixture was taken up in ethyl acetate (50 ml) and washed with water (2×50 ml). The organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuo to give an orange oil (366 mg). The product was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (30-70%) to afford the title compound as an orange gum (172 mg).
Workup
- temperatureThe reaction was cooled to room temperature
- stirringthe reaction stirred at 90° C. for 2 hours
- washwashed with water (2×50 ml)
- customThe organic layer was separated
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8233457cefd7477896680116af7e928a
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977344B2
Reaction notes
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