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

HRID 497731노트

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HRID 497731 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 3283Diethyl Ether용매

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-10f40f2b1c854700acc3831f96844b66
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949643B2

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