3,4-Dimethoxyphenylboronic acid → HCID 21955980, compound

HRID 2212876Notes

Reaction equation

HRID 2212876 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22](I)[CH:21]=3)[N:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][C:34]=1[O:35][CH3:36]>C(COC)OC.C(=O)([O-])[O-].[K+].[K+]>[NH2:1][C:2]1[S:3][C:4]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:21]=[C:22]([C:32]4[CH:31]=[CH:30][C:29]([O:28][CH3:27])=[C:34]([O:35][CH3:36])[CH:33]=4)[CH:23]=[CH:24][CH:25]=3)[N:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1

Participants

5

Reactant 2

HCID 27347023,4-Dimethoxyphenylboronic acidHCID 21955984HCID 21955984, compound

Product 1

HCID 21955980HCID 21955980, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 11430Potassium CarbonateSolvent

Procedure

A solution of N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3-iodo-phenyl)-amine (300 mg, 0.64 mmol) and 3,4-dimethoxyphenylboronic acid (122 mg, 0.66 mmol) in dimethoxyethane (8 ml) and aqueous potassium carbonate (13 ml) are stirred in the presence of tetrakis triphenylphosphine palladium (15 mg) under a nitrogen atmosphere at reflux for 1 hour. After an aqueous work-up the residue is purified by chromatography (eluent: 2:1 mixture of ethyl acetate/hexane) to give the N-[4-(2-amino-4-phenyl-thiazol-5-yl)-pyrimidin-2-yl]-N-(3′,4′-dimethoxy-biphenyl-3-yl)-amine, m.p. 236–237° C.

Workup

  1. temperatureat reflux for 1 hour
  2. customAfter an aqueous work-up the residue is purified by chromatography (eluent: 2:1 mixture of ethyl acetate/hexane)

Sources & evidence

ORD record
ord-219c5a97d8e3475fb3684c3d9bc582a9
Source dataset
uspto-grants-2006_09
Patent number
US07105517B2

Reaction notes

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