Methyl 3-aminophenylacetate → 3-{[5-(4-Methoxy-phenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenylacetic acid methyl ester

HRID 2189105Notes

Reaction equation

HRID 2189105 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:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH2:35])[CH:30]=1>ClCCl>[CH3:25][O:26][C:27](=[O:36])[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][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:30]=1

Participants

4

Reactant 2

HCID 13054266Methyl 3-aminophenylacetateHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 250953893-{[5-(4-Methoxy-phenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenylacetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Heat 300 mg (0.89 mmol) of 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine and 191.3 mg (1.16 mmol) of 3-aminophenylacetic acid methyl ester to 150° C. for 1.5 h. After cooling, add dichloromethane and filter off the resulting solid with suction, wash with dichloromethane and dry at 50° C. under high vacuum overnight. Purify the crude product by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 10:1). 273.2 mg (65.9% of theory) of the target product are obtained as a yellowish solid.

Workup

  1. temperatureAfter cooling
  2. filtrationfilter off the resulting solid with suction
  3. washwash with dichloromethane
  4. customdry at 50° C. under high vacuum overnight
  5. customPurify the crude product by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 10:1)
  6. custom273.2 mg (65.9% of theory) of the target product are obtained as a yellowish solid

Sources & evidence

ORD record
ord-bb79c25d221c4549a8c9e4ac309badbe
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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