Sodium hydride → 2-(2-Methoxy-pyrimidin-4-ylamino)-thiazole-5-carbonitrile

HRID 1241396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1241396
[H-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][N:6]=1.Cl[C:13]1[S:14][C:15]([C:18]#[N:19])=[CH:16][N:17]=1>C1COCC1>[CH3:3][O:4][C:5]1[N:10]=[C:9]([NH:11][C:13]2[S:14][C:15]([C:18]#[N:19])=[CH:16][N:17]=2)[CH:8]=[CH:7][N:6]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 1606792-O-MethylcytosineHCID 14852222-Chlorothiazole-5-carbonitrile

Produkt 1

HCID 219346202-(2-Methoxy-pyrimidin-4-ylamino)-thiazole-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A flame dried flask under argon (g) was charged with sodium hydride (33 mg, 60% dispersion, 0.83 mmol) and 1.5 mL anhydrous THF. 2-Methoxy-pyrimidin-4-ylamine (26 mg, 0.21 mmol) was added slowly. After the resulting bubbling ceased, 2-chloro-thiazole-5-carbonitrile (30 mg, 0.21 mmol) was added and the reaction was heated to reflux. After 2 hours, the reaction was cooled to room temperature, the THF was removed in vacuo, and the mixture was diluted with water and adjusted to pH 7 with 1M HCl (aq). The resulting precipitate was filtered, washed with water and air dried. The resulting solid was purified by flash column chromatography (eluted with a gradient 85:15 hexane/EtOAc to EtOAc) to give a pure sample of the title compound. 1H-NMR (300 MHz, DMSO-d6) 12.61 (s, 1H), 8.36 (d, 1H, J=6.4 Hz), 6.73 (d, 1H, J=5.6 Hz), 4.02 (s, 3H). mp>250.

Aufarbeitung

  1. customA flame dried flask under argon (g)
  2. customAfter the resulting bubbling
  3. temperaturethe reaction was heated to reflux
  4. customthe THF was removed in vacuo
  5. additionthe mixture was diluted with water
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with water and air
  8. customdried
  9. customThe resulting solid was purified by flash column chromatography (
  10. washeluted with a gradient 85:15 hexane/EtOAc to EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-71c2775553174c24b528b7d4a05c9ef2
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115597B2

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