Ethanol → 6-{[6-(4-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid ethyl ester

HRID 1926972Notes

Reaction equation

HRID 1926972 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17](Br)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:47](O)C>CC(O)=O.CC(O)=O.C1CCC([N-]C2CCCCC2)CC1.C1CCC([N-]C2CCCCC2)CC1.[Pd+2]>[CH2:1]([O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17]([C:33]3[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=3)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1)[CH3:47]

Participants

6

Reactant 4

HCID 702EthanolHCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 58016901Methyl 6-{[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoate

Product 1

HCID 580168196-{[6-(4-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 11180781trans-Bis(dicyclohexylamine)palladium(II) acetateCatalyst

Procedure

Add 3 mg (0.01 mmol) trans-bis(dicyclohexylamin)palladium(II) acetate [T. Bin, J. Org. Chem. 2004, 69, 4330-4335] to a mixture of 100 mg (0.22 mmol) 6-{[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester, 37 mg (0.27 mmol) 4-fluorophenylboronic acid and 95 mg (0.45 mmol) potassium phosphate in 5 ml ethanol, and stir, firstly for 16 h at RT and then for 3 h at 80° C. After filtering off the solid, concentrate the filtrate by vacuum evaporation. Purify the residue by preparative RP-HPLC (gradient: water/acetonitrile). 28 mg (26% of theor.) of the desired product is obtained.

Workup

  1. waitfor 3 h at 80° C
  2. filtrationAfter filtering off the solid
  3. concentrationconcentrate the filtrate
  4. customby vacuum evaporation
  5. customPurify the residue by preparative RP-HPLC (gradient: water/acetonitrile)

Sources & evidence

ORD record
ord-18d098081dc9423f9bfd9a61c6bc4bec
Source dataset
uspto-grants-2012_05
Patent number
US08183246B2

Reaction notes

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