Sodium hydride → HCID 21934676, Verbindung

HRID 1241395

Reaktionsgleichung

Reaktionsgleichung von HRID 1241395
[H-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9]([NH2:11])[CH:8]=[C:7]([O:12][CH3:13])[N:6]=1.Cl[C:15]1[S:16][C:17]([C:20]#[N:21])=[CH:18][N:19]=1>C1COCC1>[CH3:3][O:4][C:5]1[N:10]=[C:9]([NH:11][C:15]2[S:16][C:17]([C:20]#[N:21])=[CH:18][N:19]=2)[CH:8]=[C:7]([O:12][CH3:13])[N:6]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 767892,6-Dimethoxy-4-aminopyrimidineHCID 14852222-Chlorothiazole-5-carbonitrile

Produkt 1

HCID 21934676HCID 21934676, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A flame dried flask under Ar was charged with sodium hydride (110 mg, 60% dispersion, 2.77 mmol) and 3 mL anhydrous THF. 2,6-Dimethoxy-pyrimidin-4-ylamine (118 mg, 0.76 mmol) was added slowly. After the resulting bubbling ceased, 2-chloro-thiazole-5-carbonitrile (100 mg, 0.69 mmol) was added and the reaction was heated to 40° C. After several 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 3:1 hexane/EtOAc) followed by purification by reverse phase HPLC. The product was free based with sat NaHCO3 (aq) and filtered to give a pure sample of the title compound. 1H-NMR (300 MHz, DMSO-d6) 12.36 (s, 1H), 8.29 (1H, s), 6.02 (1H, s), 4.02 (s, 3H), 3.87 (s, 3H). mp>250.

Aufarbeitung

  1. customA flame dried flask under Ar
  2. customAfter the resulting bubbling
  3. temperatureAfter several hours the reaction was cooled to room temperature
  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 (eluted with 3:1 hexane/EtOAc)
  10. customfollowed by purification by reverse phase HPLC
  11. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-1fc246d709c84ae5a008638d0d65c044
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115597B2

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