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

HRID 2189082Notes

Reaction equation

HRID 2189082 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][CH:21]=[CH:20][CH:19]=2)=[CH:4][CH:3]=1.[CH3:24][O:25][C:26](=[O:36])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH2:35])[CH:30]=1>CS(C)=O>[CH3:24][O:25][C:26](=[O:36])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][C:15]2[C:10]3[C:9]([C:18]4[CH:23]=[CH:22][CH:21]=[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:30]=1

Participants

4

Reactant 2

HCID 10678961Methyl 2-(3-aminophenoxy)acetateHCID 862111966-(4-Bromophenyl)-4-chloro-5-phenylfuro[2,3-d]pyrimidine

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Heat 400 mg (1.04 mmol) of 6-(4-bromophenyl)-4-chloro-5-phenylfuro[2,3-d]pyrimidine (preparation according to WO 03/018589) and 225.5 mg (1.25 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: cyclohexane/ethyl acetate 2:1). 140 mg (25.5% of theory) of the target compound are obtained as a yellowish solid.

Workup

  1. temperatureAfter cooling
  2. filtrationfilter through silica gel (eluent: cyclohexane/ethyl acetate 2:1)
  3. custom140 mg (25.5% of theory) of the target compound are obtained as a yellowish solid

Sources & evidence

ORD record
ord-b2bb346d776b471cbb7815c5641f8839
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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