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

HRID 1814242ノート

反応式

HRID 1814242 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>CS(C)=O>[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

5

反応物 3

HCID 5558BromoformHCID 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 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
125 °C

実験手順

The product of step (a) (0.5 g) was suspended in DMSO (10 ml) and bromoform (10 ml) and the mixture was heated to 125° C. Isoamylnitrite (2 ml) was added and the mixture was stirred at 125° C. for 5 minutes before being cooled in an ice bath. Solvent was removed by evaporation under high vacuum and the residue suspended in dichloromethane (100 ml). This suspension was washed with saturated aqueous ammonium chloride (50 ml) and then filtered through a plug of celite. The filtrate was evaporated and purified by column chromatography, eluting with 10% ethyl acetate in dichloromethane to give the subtitled compound as a white solid (0.22 g).

後処理

  1. temperaturebefore being cooled in an ice bath
  2. customSolvent was removed by evaporation under high vacuum
  3. washThis suspension was washed with saturated aqueous ammonium chloride (50 ml)
  4. filtrationfiltered through a plug of celite
  5. customThe filtrate was evaporated
  6. custompurified by column chromatography
  7. washeluting with 10% ethyl acetate in dichloromethane

出典と根拠

ORDレコード
ord-9376b1745f284fb8ae1959bd43b08e0a
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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