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Potassium Carbonate → 5-methyl-4-(3-pyridinyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2(1H)-pyrimidinone hydrochloride

HRID 1514445
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1514445
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[N:8][C:7]1=[O:19].[F:20][C:21]([F:35])([F:34])[C:22]1[CH:27]=[CH:26][C:25]([C@:28]23[CH2:33][C@H:32]2[CH2:31][NH:30][CH2:29]3)=[CH:24][CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[ClH:1].[CH3:12][C:10]1[C:9]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[N:8][C:7](=[O:19])[N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:30]2[CH2:31][C@H:32]3[C@:28]([C:25]4[CH:24]=[CH:23][C:22]([C:21]([F:20])([F:35])[F:34])=[CH:27][CH:26]=4)([CH2:33]3)[CH2:29]2)[CH:11]=1
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Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 592427851-(4-Chloro-butyl)-5-methyl-4-pyridin-3-yl-1H-pyrimidin-2-oneHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

Produkt 1

HCID 687019445-methyl-4-(3-pyridinyl)-1-(4-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}butyl)-2(1H)-pyrimidinone hydrochlorideAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1-(4-chloro-butyl)-5-methyl-4-pyridin-3-yl-1H-pyrimidin-2-one (Prep12, 86 mg, 0.31 mmol), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep4, 63 mg, 0.28 mmol), KI (2 mg) and K2CO3 (43 mg, 0.31 mmol) in DMF (2 ml) was placed in a microwave oven and irradiated at 115° C. for 1 hour. After cooling, the solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and evaporated The solvent was removed under vacuum and the residue was redissolved in DCM and filtered, the filtrate was stirred in the presence of PS-isocyanate (350 mg) for 3 hours. The mixture was filtered and the solvent removed under vacuum. The crude was purified by flash chromatography with DCM-MeOH—NH4OH (99-1-0.1) to give the title compound (17 mg, 4% yield) as a free base.

Aufarbeitung

  1. customirradiated at 115° C. for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated The solvent
  7. customwas removed under vacuum
  8. dissolutionthe residue was redissolved in DCM
  9. filtrationfiltered
  10. filtrationThe mixture was filtered
  11. customthe solvent removed under vacuum
  12. customThe crude was purified by flash chromatography with DCM-MeOH—NH4OH (99-1-0.1)

Quellen und Nachweise

ORD-Eintrag
ord-b12f4a8abae5457ea46f773074605b4c
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08222266B2

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