Tetrabutylammonium Fluoride → 4-(6-Ethynyl-3-methylindazol-1-yl)pyrimidin-2-amine
Reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[C:12][Si](C)(C)C)=[CH:8][CH:9]=2)[N:4]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[N:18]=2)[N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:11]([C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH3:1])=[N:3][N:4]2[C:17]2[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[N:18]=2)=[CH:9][CH:8]=1)#[CH:12]Participants
4
Procedure
To a solution of 4-{3-methyl-6-[2-(trimethylsilyl)ethynyl]indazol-1-yl}pyrimidin-2-amine (600 mg, 1.87 mmol) in THF (15 ml) was added TBAF (2.24 mL of a 1M solution in THF, 2.24 mmol) and the reaction mixture was allowed to stand for 0.5 hr. The reaction mixture was concentrated in vacuo, DCM (5 ml) was added and the concentration repeated (×2). The crude product was purified by flash chromatography (Biotage, 3-10% methanol in DCM) to give the title intermediate as a yellow solid (300 mg): 1H NMR (500 MHz, DMSO) delta 2.58 (3H, s), 4.37 (1H, s), 7.14-6.86 (3H, m), 7.40 (1H, dd, J=8.2, 1.1 Hz), 7.85 (1H, d, J=8.2 Hz), 8.26 (1H, d, J=5.5 Hz), 8.98 (1H, s); LC-MS: m/z=+250.35 (M+H)+.