HCID 118022720, compound → Tert-butyl 4-(5-benzoylpyrimidin-2-yl)piperazine-1-carboxylate

HRID 522651Notes

Reaction equation

HRID 522651 reaction equation
CON(C)[C:4]([C:6]1[CH:7]=[N:8][C:9]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[N:10][CH:11]=1)=[O:5].C([Mg]Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1COCC1>[C:4]([C:6]1[CH:11]=[N:10][C:9]([N:12]2[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:16][CH2:17]2)=[N:8][CH:7]=1)(=[O:5])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 118022720HCID 118022720, compoundHCID 178419663HCID 178419663, compound

Product 1

HCID 118022456Tert-butyl 4-(5-benzoylpyrimidin-2-yl)piperazine-1-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 4-(5-(methoxy(methyl)carbamoyl)pyrimidin-2-yl)piperazine-1-carboxylate (2.6 g, 7.4 mmol) in dry THF (30 mL) was added benzylmagnesium bromide (1 M in THF, 29.6 mL) at 0° C. under N2, and the mixture was stirred at room temperature for 3 hours. LCMS showed the reaction was completed. The reaction mixture was quenched with 1 M HCl and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=5:1) to get tert-butyl 4-(5-benzoylpyrimidin-2-yl)piperazine-1-carboxylate (2 g, 73%) as a yellow solid. MS (ES+) C20H24N4O3 requires: 368, found: 313 [M-56+H]+.

Workup

  1. customThe reaction mixture was quenched with 1 M HCl
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (petroleum ether:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-a2bc842c87d142beb6770bec7098c56d
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

Loading…