Methyl iodide → 3-[(S)4-Boc-3-benzylpiperazinyl]-5-bromo-2-methylaminopyrazine

HRID 643348Notes

Reaction equation

HRID 643348 reaction equation
[NH2:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:10]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:9]2)=[N:6][C:5]([Br:28])=[CH:4][N:3]=1.[CH3:29]C(C)([O-])C.[K+].IC.C(OCC)(=O)C>O1CCOCC1>[C:14]([N:11]1[CH2:12][CH2:13][N:8]([C:7]2[C:2]([NH:1][CH3:29])=[N:3][CH:4]=[C:5]([Br:28])[N:6]=2)[CH2:9][C@@H:10]1[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 592622472-amino-5-bromo-3-[(S)-4-Boc-3-benzylpiperazinyl]pyrazine

Product 1

HCID 592622593-[(S)4-Boc-3-benzylpiperazinyl]-5-bromo-2-methylaminopyrazineYield 309.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-5-bromo-3-[(S)4-Boc-3-benzylpiperazinyl]pyrazine 108 (140 mg, 0.313 mmol) in anhydrous dioxane (3 mL) was added a 1 M solution of potassium t-butoxide (0.34 mL, 0.34 mmol). The reaction mixture was stirred at room temperature for 10 minutes and iodomethane (89 mg, 0.627 mmol) was added. The reaction mixture was stirred at room temperature for 2 hours. Ethyl acetate (100 mL) was added. The organic layer was washed with water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by RP-HPLC to yield the desired 3-[(S)-4-Boc-3-benzylpiperazinyl]-5-bromo-2-methylaminopyrazine 111 (45 mg, 0.97 mmol).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2 hours
  2. washThe organic layer was washed with water and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customThe organic solvent was evaporated under reduced pressure
  5. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-cc81edb18aba4267b8396430a206b9dc
Source dataset
uspto-grants-2010_04
Patent number
US07700601B2

Reaction notes

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