(4-Fluorophenyl)(2-(piperazin-1-yl)pyrimidin-5-yl)methanone → HCID 118023301, compound

HRID 1498845Notes

Reaction equation

HRID 1498845 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][C:13]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[N:14][CH:15]=2)=[O:9])=[CH:4][CH:3]=1.[CH3:22][CH2:23][Mg+].[Br-]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][C:13]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[N:14][CH:15]=2)([OH:9])[CH2:22][CH3:23])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 118022709(4-Fluorophenyl)(2-(piperazin-1-yl)pyrimidin-5-yl)methanoneHCID 178461630HCID 178461630, compound

Product 1

HCID 118023301HCID 118023301, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-fluorophenyl)(2-(piperazin-1-yl)pyrimidin-5-yl)methanone (4.0 g, 21.84 mmol) in dry THF (150 mL) was added EtMgBr (1 M in THF, 150 mL) at 0° C. under nitrogen. The mixture was stirred at RT for 3 h, then quenched with NH4Cl solution and extracted with ethyl acetate (200*3 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by combi-flash with dichloromethane:methanol=10:1 to give the title compound (440 mg, 10%) as a yellow solid. MS (ES+) C17H21FN4O requires: 316. found: 317 [M+H]+.

Workup

  1. customquenched with NH4Cl solution
  2. extractionextracted with ethyl acetate (200*3 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by combi-flash with dichloromethane

Sources & evidence

ORD record
ord-f5614aa96f1c44d9b8d93709766b96e1
Source dataset
uspto-grants-2015_12
Patent number
US09200002B2

Reaction notes

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