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

HRID 643348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 643348
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 592622593-[(S)4-Boc-3-benzylpiperazinyl]-5-bromo-2-methylaminopyrazineAusbeute 309,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cc81edb18aba4267b8396430a206b9dc
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700601B2

Notizen zur Reaktion

Wird geladen…