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

HRID 2189090Notes

Reaction equation

HRID 2189090 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=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>ClCCl>[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:2]2[C:3]3[C:10]([C:11]4[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=4)=[C:9]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[O:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:31]=1

Participants

4

Reactant 2

HCID 10678961Methyl 2-(3-aminophenoxy)acetateHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 582801213-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Heat 4.7 g (14 mmol) of 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine and 3.03 g (16.7 mmol) of 3-aminophenoxyacetic acid methyl ester to 150° C. in an oil bath for 1.5 h. After cooling, add dichloromethane to the residue and purify by means of silica gel (eluent: cyclohexane/ethyl acetate 2:1). 2.29 g (34.1% of theory) of the target compound are obtained as a pale yellowish solid.

Workup

  1. temperatureAfter cooling
  2. custompurify by means of silica gel (eluent: cyclohexane/ethyl acetate 2:1)
  3. custom2.29 g (34.1% of theory) of the target compound are obtained as a pale yellowish solid

Sources & evidence

ORD record
ord-8586f8a1b4cb41df97a51c7993e09369
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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