Potassium Carbonate → 4'-[(6-cyclopropyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]-3',5'-difluorobiphenyl-2-carbonitrile

HRID 1889384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1889384
[CH:1]1([C:4]2[S:25][C:7]3[NH:8][C:9](=[O:24])[N:10](CC4C=CC(OC)=CC=4OC)[C:11](=[O:12])[C:6]=3[CH:5]=2)[CH2:3][CH2:2]1.Br[CH2:27][C:28]1[C:33]([F:34])=[CH:32][C:31]([C:35]2[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=2)=[CH:30][C:29]=1[F:43].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:1]1([C:4]2[S:25][C:7]3[N:8]([CH2:27][C:28]4[C:33]([F:34])=[CH:32][C:31]([C:35]5[C:36]([C:41]#[N:42])=[CH:37][CH:38]=[CH:39][CH:40]=5)=[CH:30][C:29]=4[F:43])[C:9](=[O:24])[NH:10][C:11](=[O:12])[C:6]=3[CH:5]=2)[CH2:3][CH2:2]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 574605414'-(Bromomethyl)-3',5'-difluorobiphenyl-2-carbonitrileHCID 593517456-cyclopropyl-3-(2,4-dimethoxybenzyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 593515974'-[(6-cyclopropyl-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl)methyl]-3',5'-difluorobiphenyl-2-carbonitrileAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of 6-cyclopropyl-3-(2,4-dimethoxybenzyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (0.37 g), 4′-(bromomethyl)-3′,5′-difluorobiphenyl-2-carbonitrile (0.38 g), potassium carbonate (0.29 g) and acetonitrile (30 mL) was stirred at 50° C. for 2 hr. Insoluble material was filtered off, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in trifluoroacetic acid (10 mL), and the mixture was stirred at 50° C. for 2 hr. To the reaction mixture was added toluene (10 mL), and the mixture was concentrated under reduced pressure. To the obtained residue was added ethyl acetate (10 mL), and the mixture was concentrated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as a colorless solid (0.42 g, 94%).

Aufarbeitung

  1. filtrationInsoluble material was filtered off
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in trifluoroacetic acid (10 mL)
  4. stirringthe mixture was stirred at 50° C. for 2 hr
  5. additionTo the reaction mixture was added toluene (10 mL)
  6. concentrationthe mixture was concentrated under reduced pressure
  7. additionTo the obtained residue was added ethyl acetate (10 mL)
  8. concentrationthe mixture was concentrated under reduced pressure
  9. filtrationThe precipitated solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-61ebecf4c5564f1cbedb0971d5715a58
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501750B2

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