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 2189083노트

반응식

HRID 2189083 반응식
[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

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-91c805da24ba4594a493e2adef453de3
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324222B2

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