3-{[6-(4-Bromophenyl)-5-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid methyl ester → 3-[(5,6-Diphenylfuro[2,3-d]pyrimidin-4-yl)amino]phenoxyacetic acid methyl ester

HRID 2189083ノート

反応式

HRID 2189083 の反応式
[CH3:1][O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[C:14]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:20]([C:28]4[CH:33]=[CH:32][C:31](Br)=[CH:30][CH:29]=4)[O:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH:7]=1>ClCCl.C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[C:14]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:20]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[O:19][C:15]=3[N:16]=[CH:17][N:18]=2)[CH:7]=1

参加物

5

反応物 1

HCID 250951173-{[6-(4-Bromophenyl)-5-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid methyl ester

生成物 1

HCID 582802413-[(5,6-Diphenylfuro[2,3-d]pyrimidin-4-yl)amino]phenoxyacetic acid methyl ester

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Dissolve 200 mg (0.377 mmol) of 3-{[6-(4-bromophenyl)-5-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid methyl ester in 5 ml of dichloromethane and 2 ml of THF and, under argon, add 40 mg of 10% palladium on activated carbon. Stir the mixture under a hydrogen atmosphere of 3 bar gauge at RT for 3 h, before filtering off the catalyst. Wash the catalyst residue with dichloromethane and methanol, concentrate the combined filtrates under reduced pressure and chromatograph the residue on silica gel (eluent: dichloromethane/ethyl acetate 10:1). 79.1 mg (45.5% of theory) of the target compound are obtained as a colourless solid.

後処理

  1. filtrationbefore filtering off the catalyst
  2. washWash the catalyst residue with dichloromethane and methanol
  3. concentrationconcentrate the combined filtrates under reduced pressure and chromatograph the residue on silica gel (eluent: dichloromethane/ethyl acetate 10:1)
  4. custom79.1 mg (45.5% of theory) of the target compound are obtained as a colourless solid

出典と根拠

ORDレコード
ord-91c805da24ba4594a493e2adef453de3
出典データセット
uspto-grants-2012_12
特許番号
US08324222B2

反応ノート

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