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

HRID 28568

반응식

HRID 28568 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c86dbcde57e04b758ca154d53436c453
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419984B2

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