2-Fluoroethanol → N-Ethyl-2-{4-[2-(2-fluoro-ethoxy)-pyrimidin-5-ylethynyl]-phenyl}-propionamide

HRID 330841Notes

Reaction equation

HRID 330841 reaction equation
[F:1][CH2:2][CH2:3][OH:4].Cl[C:6]1[N:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]([CH3:26])[C:21]([NH:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=2)=[CH:8][N:7]=1.[H-].[Na+]>O1CCOCC1>[CH2:24]([NH:23][C:21](=[O:22])[CH:20]([C:17]1[CH:16]=[CH:15][C:14]([C:13]#[C:12][C:9]2[CH:8]=[N:7][C:6]([O:4][CH2:3][CH2:2][F:1])=[N:11][CH:10]=2)=[CH:19][CH:18]=1)[CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 97372-FluoroethanolHCID 24758Sodium hydrideHCID 866695682-[4-(2-Chloro-pyrimidin-5-ylethynyl)-phenyl]-N-ethyl-propionamide

Product 1

HCID 56929773N-Ethyl-2-{4-[2-(2-fluoro-ethoxy)-pyrimidin-5-ylethynyl]-phenyl}-propionamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To 13 mg (0.21 mmol) 2-fluoro-ethanol in 0.5 mL 1,4-dioxane are added 34 mg (0.10 mmol) 2-[4-(2-chloro-pyrimidin-5-ylethynyl)-phenyl]-N-ethyl-propionamide (XVIII.1) in 1 mL 1,4-dioxane, followed by 12 mg (0.30 mmol) sodium hydride (60% in mineral oil). The mixture is stirred at rt for 12 h. After that time, the solvent is evaporated and the residue s purified by HPLC (preparative column: Sunfire, eluent A: water+0.1% TFA, eluent B: MeOH) to yield the desired product.

Workup

  1. customAfter that time, the solvent is evaporated
  2. customthe residue s purified by HPLC (preparative column: Sunfire, eluent A: water+0.1% TFA, eluent B: MeOH)

Sources & evidence

ORD record
ord-5ebc3882721e4d1aac7410a2df8c0f3b
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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