Methyl iodide → HCID 67326839, compound

Reaction equation

[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][N:8]2[N:11]=[CH:12][C:13]([C:14]3[N:19]=[C:18]([NH:20][C@@H:21]4[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]4)[CH:17]=[CH:16][N:15]=3)=[C:7]2[CH:6]=1)#[N:4].[CH3:34]I>CN(C)C=O>[C:3]([C:5]1[CH:10]=[CH:9][N:8]2[N:11]=[CH:12][C:13]([C:14]3[N:19]=[C:18]([N:20]([CH3:34])[C@@H:21]4[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:22]4)[CH:17]=[CH:16][N:15]=3)=[C:7]2[CH:6]=1)#[N:4]

Participants

Procedure

Sodium hydride (60% dispersion in mineral oil, 102 mg, 2.55 mmol) was added to a cooled (0° C.) solution of tert-butyl (3R)-3-{[2-(5-cyanopyrazolo[1,5-a]pyridin-3-yl) pyrimidin-4-yl]amino}piperidine-1-carboxylate (Preparation 7a, 0.83 g, 1.98 mmol) in NIP-dimethylformamide (5 mL) and the reaction mixture was stirred at the same temperature for 30 minutes. Methyl iodide (0.135 mL, 2.17 mmol) was then added and the reaction mixture was stirred at room temperature for 2 hours. The solvent was concentrated in vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was separated, washed with water and brine, dried (MgSO4) and the solvent was evaporated to give the title compound (0.39 g, 80%) as a beige solid.