Sodium Bicarbonate → 5,8-Dibromo-(1,2,4)triazolo(1,5-a)pyrazine

HRID 605896

Reaktionsgleichung

Reaktionsgleichung von HRID 605896
[Br:1][C:2]1[C:3]([NH:9][CH:10]=[N:11]O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.C([O-])(O)=O.[Na+]>O>[Br:8][C:5]1[N:4]2[N:11]=[CH:10][N:9]=[C:3]2[C:2]([Br:1])=[N:7][CH:6]=1

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 178526378HCID 178526378, Verbindung

Produkt 1

HCID 497580225,8-Dibromo-(1,2,4)triazolo(1,5-a)pyrazineAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

N-(3,6-dibromo-pyrazin-2-yl)-N′-hydroxyformamidine (17.4 mg, 58.80 mmol) is treated with polyphosphoric acid (150 g) for one hour at 50° C. and then for 1.75 hours at 70° C. After cooling to room temperature, water is added to the reaction mixture. The resultant suspension is brought to pH 8 by careful addition of solid NaHCO3 in small portions. The precipitate formed is collected by filtration, washed once with 1N NaOH, three times with water and dried in vacuo. The residue is partitioned between ethyl acetate and 1N NaOH and the organic phase is washed one more time with 1N NaOH and once with brine. The organic phase is dried over MgSO4, filtered and evaporated to give the title compound (10.15 g) as a white solid. 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 8.43 (s, 1H), 8.92 (s, 1H). LCMS: Rt 2.73 min (94.2%), m/z (APCI) 277 (M+H)+.

Aufarbeitung

  1. customThe precipitate formed
  2. filtrationis collected by filtration
  3. washwashed once with 1N NaOH, three times with water
  4. customdried in vacuo
  5. customThe residue is partitioned between ethyl acetate and 1N NaOH
  6. washthe organic phase is washed one more time with 1N NaOH
  7. dry with materialThe organic phase is dried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2bd1243bb800417ea95929edc4b7e755
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07915256B2

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