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

HRID 2189088Notes

Reaction equation

HRID 2189088 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][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:27][O:28][C:29](=[O:39])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([NH2:38])[CH:33]=1>ClCCl>[CH3:27][O:28][C:29](=[O:39])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([NH:38][C:2]2[C:3]3[C:10]([C:11]4[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=4)=[C:9]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=4)[O:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:33]=1

Participants

4

Reactant 2

HCID 10678961Methyl 2-(3-aminophenoxy)acetateHCID 862112054-Chloro-5,6-bis(4-methoxyphenyl)furo[2,3-d]pyrimidine

Product 1

HCID 582802173-{[5,6-Bis(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}phenoxyacetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Heat 400 mg (1.091 mmol) of 4-chloro-5,6-bis(4-methoxyphenyl)furo[2,3-d]pyrimidine (for preparation see WO 03/018589) and 237.1 mg (1.309 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: dichloromethane/ethyl acetate 10:1). 139.3 mg (25% of theory) of the target compound are obtained as a light yellowish solid.

Workup

  1. temperatureAfter cooling
  2. custompurify by means of silica gel (eluent: dichloromethane/ethyl acetate 10:1)
  3. custom139.3 mg (25% of theory) of the target compound are obtained as a light yellowish solid

Sources & evidence

ORD record
ord-c53123e68d294bfeb36829cb2d79921f
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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