Bromoform → 4-bromo-2-[[(2,3-difluorophenyl)methyl]thio]-7(8H)-pteridinone

HRID 497731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 497731
N[C:2]1[C:11]2[N:10]=[CH:9][C:8](=[O:12])[NH:7][C:6]=2[N:5]=[C:4]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[F:22])[N:3]=1.C(Br)(Br)[Br:24].C(ON=O)CC(C)C.C(#N)C>CS(C)=O.CCOCC>[Br:24][C:2]1[C:11]2[N:10]=[CH:9][C:8](=[O:12])[NH:7][C:6]=2[N:5]=[C:4]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[F:22])[N:3]=1

Komponenten

7

Edukt 4

HCID 5558BromoformHCID 6342AcetonitrileHCID 8053Isoamyl NitriteHCID 223200814-amino-2-[[(2,3-difluorophenyl)methyl]thio]-7(8H)-pteridinone

Produkt 1

HCID 223200824-bromo-2-[[(2,3-difluorophenyl)methyl]thio]-7(8H)-pteridinone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The product of example 2, step (d) (6.0 g) was suspended in DMSO (90 ml) and bromoform (60 ml) was added and the mixture was heated to 100° C. Isopentylnitrite (25 ml) was added and the mixture stirred for 5 min. The mixture was quickly cooled in an ice bath then evaporated to leave an oil. This was repeated three times. Acetonitrile (200 ml) was added and the solid which separated was removed by filtration. The solvent was evaporated and the residue was purified by flash chromatography, eluting with dichloromethane and then 5% ethyl acetate in dichloromethane to give a yellow solid which was slurried with ether then collected. The solid was washed with ether and dried to give the subtitled compound as a colourless solid (8.74 g).

Aufarbeitung

  1. temperatureThe mixture was quickly cooled in an ice bath
  2. customthen evaporated
  3. customto leave an oil
  4. customthe solid which separated
  5. customwas removed by filtration
  6. customThe solvent was evaporated
  7. customthe residue was purified by flash chromatography
  8. washeluting with dichloromethane
  9. custom5% ethyl acetate in dichloromethane to give a yellow solid which
  10. customthen collected
  11. washThe solid was washed with ether
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-10f40f2b1c854700acc3831f96844b66
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949643B2

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