Water → HCID 67364207, compound

HRID 245655Notes

Reaction equation

HRID 245655 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([C:8]([CH:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.[Br:17]N1C(=O)CCC1=O.O>ClCCl>[Br:17][C:10]1[N:9]=[C:8]([CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([CH3:1])[C:3]=12

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 67364106HCID 67364106, compound

Product 1

HCID 67364207HCID 67364207, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 8-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazine (0.888 mmol, 193 mg) in dichloromethane (10 mL) was added N-bromosuccinimide (0.888 mmol, 158 mg) and the reaction mixture was heated at 50° C. (bath temperature) for 15 min. Dichloromethane and water were added, the organic layer separated, washed with an aqueous sodium hydrogencarbonate solution, dried (sodium sulfate) and concentrated in vacuo to afford 246 mg of 1-bromo-8-methyl-3-(tetrahydro-2H-pyran-4-yl)imidazo[1,5-a]pyrazine.

Workup

  1. customthe organic layer separated
  2. washwashed with an aqueous sodium hydrogencarbonate solution
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6da4e983d2294beebfba040ca6f083be
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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