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Lawesson's reagent → 4-thioxo-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-3,4-dihydro-2(1H)-pyrimidinone hydrochloride

HRID 12782
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 12782
[ClH:1].[F:2][C:3]([F:29])([F:28])[C:4]1[CH:9]=[CH:8][C:7]([C@:10]23[CH2:15][C@H:14]2[CH2:13][N:12]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[CH:25]=[CH:24][C:23](=O)[NH:22][C:21]2=[O:27])[CH2:11]3)=[CH:6][CH:5]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:39])=CC=1>COCCOC>[ClH:1].[S:39]=[C:23]1[CH:24]=[CH:25][N:20]([CH2:19][CH2:18][CH2:17][CH2:16][N:12]2[CH2:13][C@H:14]3[C@:10]([C:7]4[CH:8]=[CH:9][C:4]([C:3]([F:29])([F:28])[F:2])=[CH:5][CH:6]=4)([CH2:15]3)[CH2:11]2)[C:21](=[O:27])[NH:22]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 87949Lawesson's reagentHCID 686914601-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione hydrochloride

Produkt 1

HCID 866159544-thioxo-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-3,4-dihydro-2(1H)-pyrimidinone hydrochlorideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8071
1,2-Dimethoxyethane
Lösungsmittel

Versuchsvorschrift

A solution of 1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2,4(1H,3H)-pyrimidinedione (E5, 110 mg, 0.3 mmol) and Lawesson's reagent (184 mg, 0.5 mmol) in DME (2 mL) was stirred at reflux for 2 hours. The solvent was evaporated under vacuum. The crude was re-dissolved in ethyl acetate and washed with water. The organic phase was dried (Na2SO4) filtered and evaporated; the crude was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2) to give the title compound as a yellow oil (80 mg, 63% yield).

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. customThe solvent was evaporated under vacuum
  3. dissolutionThe crude was re-dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customthe crude was purified by flash chromatography with DCM-MeOH—NH4OH (98-2-0.2)

Quellen und Nachweise

ORD-Eintrag
ord-fb66b91e750f4f81a06e92bdd42c658d
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07727988B2

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