Dimethylformamide → 2-Chloro-6-[(3S)-3-methylmorpholin-4-yl]-9-(2,2,2-trifluoroethyl)-9H-purine
Reaction equation
[F:1][C:2]([F:13])([F:12])[CH2:3]OS(C(F)(F)F)(=O)=O.CN(C)C=O.[Cl:19][C:20]1[N:28]=[C:27]2[C:23]([N:24]=[CH:25][NH:26]2)=[C:22]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]2[CH3:35])[N:21]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:19][C:20]1[N:28]=[C:27]2[C:23]([N:24]=[CH:25][N:26]2[CH2:3][C:2]([F:13])([F:12])[F:1])=[C:22]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][C@@H:30]2[CH3:35])[N:21]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
2,2,2-Trifluoroethyltrifluoromethyl sulfonate (83 μl, 0.57 mmol) was added to an N,N-dimethylformamide (5 ml) suspension of 2-chloro-6-[(3S)-3-methylmorpholin-4-yl]-9H-purine (132 mg, 0.52 mmol) and potassium carbonate (86 mg, 0.62 mmol) with ice cooling. The reaction mixture was stirred at 50° C. for 2 hours and returned to room temperature. Water was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate and, after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (30% ethyl acetate:hexane) to give the title compound (133 mg, 76%) as a solid.
Workup
- customreturned to room temperature
- extractionthe resulting mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationafter filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by flash silica gel column chromatography (30% ethyl acetate:hexane)
Sources & evidence
- ORD record
- ord-1902e49eae69493d8a55f4100beae7d2
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097622B2
Reaction notes
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