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Ammonia → 5-Bromo-2-(trifluoromethyl)pyrimidine

HRID 734336
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 734336
[F-].[K+].[F:3][C:4]([Si](C)(C)C)([F:6])[F:5].[Br:11][C:12]1[CH:13]=[N:14][C:15](I)=[N:16][CH:17]=1.N>CN1C(=O)CCC1.CN(C)C=O>[Br:11][C:12]1[CH:13]=[N:14][C:15]([C:4]([F:6])([F:5])[F:3])=[N:16][CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 70066515-Bromo-2-iodopyrimidine

Produkt 1

HCID 336979635-Bromo-2-(trifluoromethyl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228Dimethylformamide
Lösungsmittel
HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A mixture of potassium fluoride (1.77 g) and cuprous iodide (5.79 g) was stirred and heated together using a heat gun under vacuum (˜1 mm) for 20 min. After cooling, dimethyl formamide (20 ml) and N-methyl pyrrolidinone (20 ml) were added followed by (trifluoromethyl)trimethylsilane (4.1 ml) and 5-bromo-2-iodopyrimidine (6.5 g). The mixture was stirred at rt for 5 h and then the brown solution was poured into 6N ammonia solution. The product was extracted into ethyl acetate and the extracts were washed with sodium bicarbonate solution and brine and then dried (Na2SO4) and evaporated. Chromatography on silica gel (elution with 20-50% dichloromethane in pentane) gave the title compound (D30) as a white solid (2.4 g). 1H NMR (CDCl3): 8.97 (2H, s).

Aufarbeitung

  1. temperatureheated together
  2. customfor 20 min
  3. temperatureAfter cooling
  4. stirringThe mixture was stirred at rt for 5 h
  5. extractionThe product was extracted into ethyl acetate
  6. washthe extracts were washed with sodium bicarbonate solution and brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8a3c2b0fa54640a5b372585a9998c897
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07592347B2

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