Methyl 2-(3-aminophenoxy)acetate → 3-{[6-(4-Bromophenyl)-5-(4-fluorophenyl)furo[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid methyl ester

HRID 2189085Notes

Reaction equation

HRID 2189085 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:17][C:11]3[N:12]=[CH:13][N:14]=[C:15](Cl)[C:10]=3[C:9]=2[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[CH3:25][O:26][C:27](=[O:37])[CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([NH2:36])[CH:31]=1>CS(C)=O>[CH3:25][O:26][C:27](=[O:37])[CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([NH:36][C:15]2[C:10]3[C:9]([C:18]4[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=4)=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=4)[O:17][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:31]=1

Participants

4

Reactant 2

HCID 10678961Methyl 2-(3-aminophenoxy)acetateHCID 862111986-(4-Bromophenyl)-4-chloro-5-(4-fluorophenyl)furo[2,3-d]pyrimidine

Product 1

HCID 582801093-{[6-(4-Bromophenyl)-5-(4-fluorophenyl)furo[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid methyl esterYield 44.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Heat 400 mg (0.991 mmol) of 6-(4-bromophenyl)-4-chloro-5-(4-fluorophenyl)furo[2,3-d]pyrimidine (for preparation see WO 03/018589) and 215.5 mg (1.19 mmol) of 3-aminophenoxyacetic acid methyl ester to 150° C. in an oil bath for 1.5 h. After cooling, take up the residue in DMSO and filter through silica gel (eluent: dichloromethane/ethyl acetate 10:1). 242 mg of a mixture are isolated, which is purified by preparative HPLC. 120 mg (15% of theory) of the target compound are obtained as a colourless solid.

Workup

  1. temperatureAfter cooling
  2. filtrationfilter through silica gel (eluent: dichloromethane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-b29d87358ed7478182819225596358f7
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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