Ethyl 3-(3-aminophenyl)acrylate → (2E)-3-(3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenyl)acrylic acid ethyl ester

HRID 2189098Notes

Reaction equation

HRID 2189098 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.[NH2:25][C:26]1[CH:27]=[C:28]([CH:36]=[CH:37][CH:38]=1)/[CH:29]=[CH:30]/[C:31]([O:33][CH2:34][CH3:35])=[O:32]>ClCCl>[CH2:34]([O:33][C:31](=[O:32])/[CH:30]=[CH:29]/[C:28]1[CH:36]=[CH:37][CH:38]=[C:26]([NH:25][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:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[O:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH:27]=1)[CH3:35]

Participants

4

Reactant 2

HCID 5355747Ethyl 3-(3-aminophenyl)acrylateHCID 580168154-Chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine

Product 1

HCID 25095120(2E)-3-(3-{[5-(4-Methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]amino}phenyl)acrylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Heat 500 mg (1.85 mmol) of 4-chloro-5-(4-methoxyphenyl)-6-phenylfuro[2,3-d]pyrimidine and 369 mg (1.93 mmol) of ethyl 3-amino-trans-cinnamate to 150° C. for 1.5 h. After cooling, add dichloromethane and purify the crude product by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 20:1). 539.5 mg (73.9% of theory) of the target product are obtained as a yellowish solid.

Workup

  1. temperatureAfter cooling
  2. custompurify the crude product by chromatography on silica gel (eluent: dichloromethane/ethyl acetate 20:1)
  3. custom539.5 mg (73.9% of theory) of the target product are obtained as a yellowish solid

Sources & evidence

ORD record
ord-b34bfcff25e640f7b7bc7ab973969c27
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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