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

HRID 522677Notes

Reaction equation

HRID 522677 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-39b0c0e34764480d997e3b81d7da985c
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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