1-(2-(Piperazin-1-yl)pyrimidin-5-yl)ethanone hydrochloride → 1-(4-Fluorophenyl)-1-(2-(piperazin-1-yl)pyrimidin-5-yl)ethanol

HRID 1498854Notes

Reaction equation

HRID 1498854 reaction equation
[N:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([Mg]Br)=[CH:19][CH:18]=1>C1COCC1>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:13]([C:10]2[CH:11]=[N:12][C:7]([N:1]3[CH2:2][CH2:3][NH:4][CH2:5][CH2:6]3)=[N:8][CH:9]=2)([OH:15])[CH3:14])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 1180224421-(2-(Piperazin-1-yl)pyrimidin-5-yl)ethanone hydrochlorideHCID 178418676HCID 178418676, compound

Product 1

HCID 1180232651-(4-Fluorophenyl)-1-(2-(piperazin-1-yl)pyrimidin-5-yl)ethanolYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-(piperazin-1-yl)pyrimidin-5-yl)ethanone (1.8 g, 8.73 mmol) in dry THF (100 mL) was added (4-fluorophenyl)magnesium bromide (1 M in THF, 87.3 mL) at 0° C. under N2. The mixture was stirred at RT for 3 h, then quenched with ammonium chloride solution and extracted with dichloromethane (300 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by Combi-flash (dicholomethane:methanol=10:1) to give the title compound (1.02 g, 38%) as a yellow solid.

Workup

  1. customquenched with ammonium chloride solution
  2. extractionextracted with dichloromethane (300 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by Combi-flash (dicholomethane:methanol=10:1)

Sources & evidence

ORD record
ord-62da16d9816a47ee9c48f9882f01f051
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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