2-Aminopyrimidine → 2-Methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine

HRID 241454

Reaktionsgleichung

Reaktionsgleichung von HRID 241454
Br[CH:2]([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=O.[NH2:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1.C(=O)(O)[O-].[Na+]>CC(O)C>[CH3:15][C:2]1[N:16]=[C:17]2[N:22]=[CH:21][CH:20]=[CH:19][N:18]2[C:3]=1[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 79782-AminopyrimidineHCID 516892Sodium BicarbonateHCID 104238192-Bromo-1-(4-(trifluoromethyl)phenyl)propan-1-one

Produkt 1

HCID 710597752-Methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidineAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

Stir a mixture of 2-bromo-1-[4-(trifluoromethyl)phenyl]propan-1-one (500 g, 1.78 mol, 1 equiv), IPA (5 L), 2-aminopyrimidine (205 g, 2.13 mol, 1.2 equiv), and sodium bicarbonate (298.8 g, 3.55 mol, 2 equiv) in a thermally controlled reactor at 80° C. for 18 hours. Cool the suspension, and concentrate in vacuo. Dilute the resulting mixture with DCM (5 L), and the wash with brine (2 L). Re-extract the brine wash with DCM (2.5 L); combine all the organic extracts; dry over MgSO4; filter; collect the filtrate; and concentrate the filtrate under reduced pressure to a red gum. Slurry the resulting red gum in Et2O (1.5 L); filter; and collect the solid. Air dry the solid for 45 min to give the product as a fine off-white solid (108 g, 22% yield). ES/MS (m/z) 278 (M+1).

Aufarbeitung

  1. temperatureCool the suspension
  2. concentrationconcentrate in vacuo
  3. additionDilute the resulting mixture with DCM (5 L)
  4. washthe wash with brine (2 L)
  5. washRe-extract the brine wash with DCM (2.5 L)
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. customcollect the filtrate
  9. concentrationand concentrate the filtrate under reduced pressure to a red gum
  10. filtrationfilter
  11. customand collect the solid
  12. customAir dry the solid for 45 min

Quellen und Nachweise

ORD-Eintrag
ord-4db7d2b3cd934d60b663f3ace5d85a5f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648200B2

Verknüpfte Notizen

Wird geladen…