Potassium Carbonate → N2-Butyl-8-(methyloxy)-9-[2-[(3R)-tetrahydro-3-furanyl]ethyl}-9H-Purine-2,6-diamine
Reaction equation
[CH2:1]([NH:5][C:6]1[NH:14][C:13]2[C:9]([N:10]=[C:11]([O:15][CH3:16])[N:12]=2)=[C:8]([NH2:17])[N:7]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][C@@H:27]1[CH2:31][CH2:30][O:29][CH2:28]1>CN(C=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[CH2:25][CH2:26][C@@H:27]2[CH2:31][CH2:30][O:29][CH2:28]2)=[C:8]([NH2:17])[N:7]=1)[CH2:2][CH2:3][CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
N2-Butyl-8-(methyloxy)-3H-purine-2,6-diamine (157 mg, 0.447 mmol) was heated in dry DMF (3 ml) with potassium carbonate (232 mg, 1.675 mmol) at 60° C. for one hour. (3S)-3-(2-Bromoethyl)tetrahydrofuran (100 mg, 0.558 mmol) in dry DMF (2 ml) was added and the mixture stirred and heated to 60° C. under nitrogen for 4 hours. The mixture was cooled to room temperature, quenched into water (40 ml) and extracted with ethyl acetate (3×25 ml). The organic extracts were combined, dried by passage through a hydrophobic frit and concentrated under vacuum. The residue was dissolved in 1:1 MeOH:DMSO and purified by mass directed autopreparation. The desired fractions were combined and concentrated using a nitrogen blowdown unit to give the title compound as a white solid (119 mg).
Workup
- temperatureThe mixture was cooled to room temperature
- customquenched into water (40 ml)
- extractionextracted with ethyl acetate (3×25 ml)
- customdried by passage through a hydrophobic frit
- concentrationconcentrated under vacuum
- dissolutionThe residue was dissolved in 1:1 MeOH
- customDMSO and purified by mass
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-50c59ce09a894f1e973595b425e41c72
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977344B2
Reaction notes
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