Ethanol → 2-{4-[1-(2-Ethoxy-pyrimidin-4-yl)-piperidin-4-yl]-phenyl}-N-ethyl-propionamide

HRID 409739Notes

Reaction equation

HRID 409739 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]([CH3:26])[C:21]([NH:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[CH2:27]([OH:29])[CH3:28].[H-].[Na+]>O1CCOCC1>[CH2:27]([O:29][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[CH:19]=[CH:18][C:17]([CH:20]([CH3:26])[C:21]([NH:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1)[CH3:28]

Participants

5

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 866861182-{4-[1-(2-Chloro-pyrimidin-4-yl)-piperidin-4-yl]-phenyl}-N-ethyl-propionamide

Product 1

HCID 715761462-{4-[1-(2-Ethoxy-pyrimidin-4-yl)-piperidin-4-yl]-phenyl}-N-ethyl-propionamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 80 mg (0.22 mmol) 2-{4-[1-(2-chloro-pyrimidin-4-yl)-piperidin-4-yl]-phenyl}-N-ethyl-propionamide (XII.1) and 25 μL (0.43 mmol) ethanol in 1 mL 1,4-dioxane are added 26 mg (0.64 mmol) sodium hydride (60%) at 0° C. The mixture is stirred for 12 h at rt. After that time, the mixture is directly purified by HPLC (XBridge 10 μM; water, 0.3% NH4OH/MeOH) to yield the desired product.

Workup

  1. customAfter that time, the mixture is directly purified by HPLC (XBridge 10 μM; water, 0.3% NH4OH/MeOH)

Sources & evidence

ORD record
ord-ed2d871df26041b28254cf036fb173a0
Source dataset
uspto-grants-2014_06
Patent number
US08759528B2

Reaction notes

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