Ammonium Chloride → HCID 178462869, Verbindung

HRID 1893912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1893912
[NH2:1][C:2]1[N:3]=[C:4]([CH3:17])[C:5]2[CH:11]=[C:10]([C:12]#[CH:13])[C:9](=[O:14])[N:8]([CH2:15][CH3:16])[C:6]=2[N:7]=1.[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].[NH4+]>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([CH3:17])[C:5]2[CH:11]=[C:10]([C:12]3[NH:20][N:19]=[N:18][CH:13]=3)[C:9](=[O:14])[N:8]([CH2:15][CH3:16])[C:6]=2[N:7]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 576069672-amino-8-ethyl-6-ethynyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one

Produkt 1

HCID 178462869HCID 178462869, VerbindungAusbeute 6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Anhydrous DMF (5.0 mL) was added to a flask charged with 2-amino-8-ethyl-6-ethynyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (0.204 g, 0.894 mmol), sodium azide (0.070 g, 1.07 mmol), and ammonium chloride (0.057 g, 1.07 mmol). The reaction was capped under nitrogen and heated to 120° C. After 48 h, the reaction was cooled to room temperature and concentrated in vacuo. The residue was purified on reverse phase HPLC (acetonitrile: water 0.1% TFA, 20-60% gradient). The fractions containing product were collected and concentrated to one half volume and poured into saturated NaHCO3 (50 mL). The aqueous phase was washed trice with ethyl acetate (50 mL) and dried over Na2SO4, filtered, and concentrated in vacuo. The residue was triturated with methylene chloride and ethyl acetate to afford 2-amino-8-ethyl-4-methyl-6-(1H-1,2,3-triazol-5-yl)pyrido[2,3-d]pyrimidin-7(8H)-one (14 mg, 6% yield) as a light yellow solid: 1H NMR (400 MHz, DMSO-d6): δ 8.55 (bs, 1H), 8.41 (bs, 1H), 7.32 (bs, 2H), 4.37 (q, J=7.2 Hz, 2H), 2.60 (s, 3H), 1.21 (t, J=7.2 Hz, 3H); MS (EI) for C12H13N7O: 272.0 (MH+).

Aufarbeitung

  1. customThe reaction was capped under nitrogen
  2. temperaturethe reaction was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified on reverse phase HPLC (acetonitrile: water 0.1% TFA, 20-60% gradient)
  5. additionThe fractions containing product
  6. customwere collected
  7. concentrationconcentrated to one half volume
  8. additionpoured into saturated NaHCO3 (50 mL)
  9. washThe aqueous phase was washed trice with ethyl acetate (50 mL)
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue was triturated with methylene chloride and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7e1eecf9d48442d88b455a27bb9a8644
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513266B2

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