1-Methylpiperazine → 8-(4-Methyl-piperazin-1-yl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazine

HRID 1186496Notes

Reaction equation

HRID 1186496 reaction equation
Cl[C:2]1[C:3]2[N:4]([C:8]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=3)=[CH:9][N:10]=2)[CH:5]=[CH:6][N:7]=1.[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(N(C(C)C)CC)(C)C>CC(O)C>[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:2]2[C:3]3[N:4]([C:8]([C:11]4[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=4)=[CH:9][N:10]=3)[CH:5]=[CH:6][N:7]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 866709158-Chloro-3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazine

Product 1

HCID 682267268-(4-Methyl-piperazin-1-yl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 8-chloro-3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazine (from Example 44 supra) (1.36 g, 4.91 mmol) in iPrOH (100 mL) was added 1-methylpiperazine (0.64 g, 6.38 mmol) followed by diisopropylethylamine (0.82 g, 6.38 mmol). The reaction mixture was stirred at reflux for 15 hours and the solvent was removed under reduced pressure. The residue was extracted with dichloromethane (150 mL) and washed with water (3×25 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford 8-(4-methyl-piperazin-1-yl)-3-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[1,2-a]pyrazine. (Yield 1.4 g, 83.7%). LC-MS: [M+H]+ 342.

Workup

  1. temperatureat reflux for 15 hours
  2. customthe solvent was removed under reduced pressure
  3. extractionThe residue was extracted with dichloromethane (150 mL)
  4. washwashed with water (3×25 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5adcb3fefeea48ee902cce10c6fcf5fe
Source dataset
uspto-grants-2014_03
Patent number
US08673905B2

Reaction notes

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