TBAF tetrahydrofuran → (S)-N2-[1-(4-fluorophenyl)ethyl]-6-(oxazol-5-yl)-N4-(pyrazin-2-yl)pyrimidine-2,4-diamine
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([NH:17][C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:13]([C:24]3[O:28][C:27]([Si](C(C)C)(C(C)C)C(C)C)=[N:26][CH:25]=3)[N:12]=2)[CH3:9])=[CH:4][CH:3]=1.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([NH:17][C:18]3[CH:23]=[N:22][CH:21]=[CH:20][N:19]=3)[CH:14]=[C:13]([C:24]3[O:28][CH:27]=[N:26][CH:25]=3)[N:12]=2)[CH3:9])=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
122 mg of (S)—N2-[1-(4-fluorophenyl)ethyl]-N4-(pyrazin-2-yl)-6-[2-(triisopropylsilyl)oxazol-5-yl]pyrimidine-2,4-diamine was dissolved in 1.2 ml of tetrahydrofuran, and 0.5 ml of 1 M tetrabutylammonium fluoride tetrahydrofuran solution was added. The reaction solution was stirred at room temperature for 20 min, and then diluted with ethyl acetate. The solution was washed in turn with water and brine and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 60 mg of (S)—N2-[1-(4-fluorophenyl)ethyl]-6-(oxazol-5-yl)-N4-(pyrazin-2-yl)pyrimidine-2,4-diamine as white powder. The obtained compound was subjected to hydrochlorination using a conventional method to obtain 45 mg of the objective compound as pale orange powder.
Workup
- washThe solution was washed in turn with water and brine
- dry with materialdried over magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-524a4789ad874731bd5e415214cf38f6
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673891B2
Reaction notes
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