Diisopropyl Ether → N-{4-[6-amino-5-cyano-2-(6-methylpyridin-2-ylmethylsulfanyl)pyrimidin-4-yl]phenyl}acetamide

HRID 1668539

Reaktionsgleichung

Reaktionsgleichung von HRID 1668539
[NH2:1][C:2]([NH2:4])=[S:3].[C:5]([C:7]([C:19]#[N:20])=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=1)#[N:6].[C:21](=O)(O)[O-].[Na+].[CH2:26]1[C:31](=O)[N:30](Br)[C:28](=O)[CH2:27]1.[CH:34](OC(C)C)(C)[CH3:35]>C(O)C>[NH2:6][C:5]1[N:4]=[C:2]([S:3][CH2:21][C:31]2[CH:26]=[CH:35][CH:34]=[C:28]([CH3:27])[N:30]=2)[N:1]=[C:8]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:18])[CH3:17])=[CH:11][CH:10]=2)[C:7]=1[C:19]#[N:20]

Komponenten

7

Edukt 5

HCID 7914Diisopropyl EtherHCID 33296N-(4-(2,2-Dicyanoethenyl)phenyl)acetamideHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 2723790Thiourea

Produkt 1

HCID 11581892N-{4-[6-amino-5-cyano-2-(6-methylpyridin-2-ylmethylsulfanyl)pyrimidin-4-yl]phenyl}acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

The portion (4.56 g) was dissolved in 50 mL of ethanol, 1.72 g of thiourea was added to the solution, and the mixture was heated to reflux for 1 hour. Next, to the reaction solution added 20 mL of ethanol and the solution was cooled, and further 4.79 g of N-[4-(2,2-dicyanovinyl)phenyl]acetamide and 3 g of sodium bicarbonate were added thereto, and then the mixture was heated to reflux for 1.5 hours. After the reaction solution was allowed to cool, 2.02 g of NBS was added to the solution, and the mixture was heated to reflux for 30 minutes. After reaction solution was allowed to cool, furthermore diisopropyl ether was added thereto, and the inorganic material precipitated was filtrated off, then the filtrate was again concentrated and dissolved in ethanol. Saturated aqueous sodium bicarbonate was added to the solution and the resulting crystal was filtrated, washed with water and ethanol, and then dried under reduced pressure to give 3.2 g of N-{4-[6-amino-5-cyano-2-(6-methylpyridin-2-ylmethylsulfanyl)pyrimidin-4-yl]phenyl}acetamide as a white powder.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperaturethe solution was cooled
  4. temperaturethe mixture was heated
  5. temperatureto reflux for 1.5 hours
  6. temperatureto cool
  7. temperaturethe mixture was heated
  8. temperatureto reflux for 30 minutes
  9. customAfter reaction solution
  10. temperatureto cool
  11. customthe inorganic material precipitated
  12. filtrationwas filtrated off
  13. concentrationthe filtrate was again concentrated
  14. dissolutiondissolved in ethanol
  15. additionSaturated aqueous sodium bicarbonate was added to the solution
  16. filtrationthe resulting crystal was filtrated
  17. washwashed with water and ethanol
  18. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9b5a915edc4941cb944ab391151d2d46
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989446B2

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