[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

HRID 928559Notes

Reaction equation

HRID 928559 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]=1

Participants

4

Reactant 2

HCID 89579549[1-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-4-piperidyl]methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 895795321-(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)piperidine-4-carbaldehydeYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. washeluted through a pad of silica (eluting ethyl acetate)
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-7145e3d90730433680a51dc2768e066b
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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