Tetrabutylammonium Fluoride → 2-(4-Chloro-phenyl)-N-{5-[7-(3-hydroxymethyl-oxetan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl]-pyridin-3-yl}-acetamide
Reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1([N:12]2[C:16]3[N:17]=[CH:18][N:19]=[CH:20][C:15]=3[C:14]([C:21]([C:23]3[CH:24]=[C:25]([NH:29][C:30](=[O:39])[CH2:31][C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=4)[CH:26]=[N:27][CH:28]=3)=[O:22])=[CH:13]2)[CH2:11][O:10][CH2:9]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][C:30]([NH:29][C:25]2[CH:26]=[N:27][CH:28]=[C:23]([C:21]([C:14]3[C:15]4[CH:20]=[N:19][CH:18]=[N:17][C:16]=4[N:12]([C:8]4([CH2:7][OH:6])[CH2:11][O:10][CH2:9]4)[CH:13]=3)=[O:22])[CH:24]=2)=[O:39])=[CH:33][CH:34]=1Participants
4
Procedure
N-(5-{7-[3-(tert-Butyl-dimethyl-silanyloxymethyl)-oxetan-3-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl}-pyridin-3-yl)-2-(4-chloro-phenyl)-acetamide (Preparation 203 mg, 0.059 mmol) was dissolved in dry THF (0.5 mL) and tetrabutylammonium fluoride (0.065 mL of a 1M solution in THF, 0.065 mmol.) was added. The reaction was stirred for 30 min at room temperature. The mixture was partitioned between water and EtOAc. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were concentrated and purified by preparative HPLC to give the title compound in quantitative yield 28 mg.