Tetrabutylammonium Fluoride → HCID 86686629, compound
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH3:19])([CH3:18])[C:16]#[N:17])=[CH:11][CH:10]=2)[C:5]([C:20]#[C:21][CH2:22][OH:23])=[CH:4][N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:20]=[C:21]([CH2:22][OH:23])[N:8]([C:9]3[CH:10]=[CH:11][C:12]([C:15]([CH3:19])([CH3:18])[C:16]#[N:17])=[CH:13][CH:14]=3)[C:6]=2[N:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(4-(2-chloro-5-(3-hydroxyprop-1-ynyl)pyrimidin-4-ylamino)phenyl)-2-methylpropanenitrile was reacted with a solution of 1M tetrabutylammonium fluoride in THF (5.85 mL, 5.85 mmol) diluted to 10 mL with additional dry THF for 1.5 hr at 60° C. Analytical LC indicates the reaction is complete (minimal shift in retention time). Volatiles were removed and the residue taken up into ethyl acetate. Organics were washed with water, brine then dried over sodium sulfate. Volatiles were removed and the residue purified by NPLC (10-75% ethyl acetate in Heptane, Analogix) to yield the desired product (589 mg, 68%). MS 327.3 m/z (M+H)