Sodium Carbonate → 5-Bromo-4-chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-2ylamine

HRID 28568

反応式

HRID 28568 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([Br:9])=[C:4](Cl)[N:3]=1.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16](B(O)O)[CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(COC)OC>[Br:9][C:5]1[C:6]([Cl:8])=[N:7][C:2]([NH2:1])=[N:3][C:4]=1[C:14]1[CH:13]=[C:12]([Cl:11])[CH:17]=[CH:16][C:15]=1[O:21][CH3:22]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 6182885-Bromo-4,6-dichloropyrimidin-2-amineHCID 27357515-Chloro-2-methoxyphenylboronic acid

生成物 1

HCID 860043285-Bromo-4-chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-2ylamine収率 23%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a mixture of 2-amino-4,6-dichloro-5-bromo-pyrimidine (1.22 g, 5.0 mmol), 5-chloro-2-methoxy-phenyl boronic acid (1.03 g, 5.5 mmol), palladium (II) acetate (0.17 g, 0.75 mmol) and triphenylphosphine (0.393 g, 1.5 mmol) was added a solution of sodium carbonate (3.18 g, 30 mmol) in water (20 ml) followed by glyme (100 ml). The mixture was stirred under an argon atmosphere at room temperature for 72 hours. Filtration and concentration of the filtrate yielded a residue which was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3) to provide 5-bromo-4-chloro-6-(5-chloro-2-methoxy-phenyl)-pyrimidin-2ylamine (0.40 g, 23% yield) as a beige powder.

後処理

  1. filtrationFiltration and concentration of the filtrate
  2. customyielded a residue which
  3. customwas purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3)

出典と根拠

ORDレコード
ord-c86dbcde57e04b758ca154d53436c453
出典データセット
uspto-grants-2008_09
特許番号
US07419984B2

関連ノート

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