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

HRID 1814238ノート

反応式

HRID 1814238 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
100 °C

実験手順

The product of 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).

後処理

  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

出典と根拠

ORDレコード
ord-e4193ce86b66477ca2d545426fdb5a3e
出典データセット
uspto-grants-2005_04
特許番号
US06875868B2

反応ノート

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