[1-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-4-piperidyl]methanol → 1-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)piperidine-4-carbaldehyde
Reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl:12][C:13]1[N:14]=[C:15]([N:28]2[CH2:33][CH2:32][CH:31]([CH2:34][OH:35])[CH2:30][CH2:29]2)[C:16]2[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:20][S:19][C:17]=2[N:18]=1>ClCCl>[Cl:12][C:13]1[N:14]=[C:15]([N:28]2[CH2:29][CH2:30][CH:31]([CH:34]=[O:35])[CH2:32][CH2:33]2)[C:16]2[C:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:20][S:19][C:17]=2[N:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Pyridinium chlorochromate (898 mg, 4.17 mmol) was added to a stirred solution of [1-(2-chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-4-piperidyl]methanol (1 g, 2.78 mmol) in dry dichloromethane (ml) at room temperature. The resulting mixture was stirred for 2 h and then eluted through a pad of silica (eluting ethyl acetate). The solvent was evaporated to give the 1-(2-chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)piperidine-4-carbaldehyde as a pale yellow solid (1 g, quantitative yield). Product was used in the subsequent reaction without further purification. LCMS: (M+H)+358, RT=4.98 min.