Tetrabutylammonium Fluoride → 2-[5-(3-Ethynyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propan-2-ol
Reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[CH:11]=[C:12]([C:22]3[S:26][C:25]([C:27]([OH:30])([CH3:29])[CH3:28])=[N:24][CH:23]=3)[CH:13]=[C:14]([C:16]#[C:17][Si](C)(C)C)[CH:15]=2)[N:4]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:16]([C:14]1[CH:13]=[C:12]([C:22]2[S:26][C:25]([C:27]([OH:30])([CH3:28])[CH3:29])=[N:24][CH:23]=2)[CH:11]=[C:10]([NH:9][C:5]2[N:4]=[C:3]([C:2]([F:32])([F:31])[F:1])[CH:8]=[CH:7][N:6]=2)[CH:15]=1)#[CH:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the product of Step 2 (35 mg, 0.073 mmol) in THF (1.0 mL) was added TBAF (1.0 M in THF, 0.44 mL, 0.44 mmol) and the mixture was stirred at room temperature for 90 minutes. The mixture was concentrated in vacuo, then purified by chromatography on silica gel (80:20 to 30:70, hexanes:ethyl acetate) to provide 22 mg (0.054 mmol, 74%) of 2-[5-(3-ethynyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]propan-2-ol as a white solid. MS ESI: [M+H]+ m/z 405.1. 1H NMR (400 MHz, CDCl3): δ 8.68 (d, J=4.9 Hz, 1H); 8.06 (s, 1H); 7.88 (s, 1H); 7.69-7.59 (m, 2H); 7.38 (s, 1H); 7.09 (d, J=4.9 Hz, 1H); 3.20 (s, 1H); 2.05 (s, 1H); 1.73 (s, 6H). rhSYK activity=+++
Workup
- concentrationThe mixture was concentrated in vacuo
- custompurified by chromatography on silica gel (80:20 to 30:70, hexanes:ethyl acetate)
Sources & evidence
- ORD record
- ord-df5189df8e474d2fb65fb0582481cdd5
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759366B2
Reaction notes
Loading…