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Dimethylformamide → Ainuovirine

HRID 1643356
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1643356
Br[C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([CH3:21])[CH:20]=1)[C:5]([C:7]1[NH:12][C:11](=[O:13])[NH:10][C:9](=[O:14])[C:8]=1[CH:15]([CH3:17])[CH3:16])=[O:6].C([O-])([O-])=O.[K+].[K+].I[CH2:29][CH3:30].[CH3:31][N:32](C=O)C>O.[C-]#N.[Zn+2].[C-]#N.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:29]([N:12]1[C:7]([C:5]([C:4]2[CH:3]=[C:2]([CH:20]=[C:19]([CH3:21])[CH:18]=2)[C:31]#[N:32])=[O:6])=[C:8]([CH:15]([CH3:17])[CH3:16])[C:9](=[O:14])[NH:10][C:11]1=[O:13])[CH3:30]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 577518946-(3-bromo-5-methylbenzoyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 25215428AinuovirineAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11186
Zinc cyanide (Zn(CN)2)
Katalysator
HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Katalysator
HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

To a stirred solution of 6-(3-bromo-5-methylbenzoyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione (2.14 kg, 6.09 mol) in anhydrous DMF (5 L) under nitrogen, were added zinc cyanide (428 g), DPPF (73 g), and Pd2dba3 (56 g), in this order. The mixture was heated to 110-120° C. and stirred vigorously for 2 hours. After cooling to room temperature, K2CO3 (1.88 kg) and iodoethane (1.15 L, 14.31 mol) were added to the mixture. The mixture was heated to 60-65° C. and stirred for 18 hours. After cooling to room temperature, the mixture was diluted with water (20 L). The precipitate was collected by filtration, washed with water (10 L) and then dissolved in dichloromethane (30 L). The solution was washed with water (10 L), 2N-HCl (10 L), dried with anhydrous magnesium sulfate (1 kg), and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/dichloromethane, 1:9) to afford 3-(3-ethyl-5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyl)-5-methylbenzonitrile (951 g, 2.92 mol, 48%) as a white solid.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. temperatureThe mixture was heated to 60-65° C.
  3. stirringstirred for 18 hours
  4. temperatureAfter cooling to room temperature
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water (10 L)
  7. dissolutiondissolved in dichloromethane (30 L)
  8. washThe solution was washed with water (10 L), 2N-HCl (10 L)
  9. dry with materialdried with anhydrous magnesium sulfate (1 kg)
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by silica gel column chromatography (eluent: ethyl acetate/dichloromethane, 1:9)

Quellen und Nachweise

ORD-Eintrag
ord-487be0a312ac42a9bfcf5e9d82d5198a
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08119800B2

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