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 2189083Notes

Reaction equation

HRID 2189083 reaction equation
[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

Participants

5

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-91c805da24ba4594a493e2adef453de3
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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