Sodium Carbonate → 4-Chloro-6-(2,5-dichloro-phenyl)-pyrimidin-2-yl-amine

HRID 28536

반응식

HRID 28536 반응식
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH2:9])[N:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1B(O)O.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>[Cl:8][C:6]1[CH:7]=[C:2]([C:15]2[CH:16]=[C:11]([Cl:10])[CH:12]=[CH:13][C:14]=2[Cl:17])[N:3]=[C:4]([NH2:9])[N:5]=1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 655222-Amino-4,6-dichloropyrimidineHCID 27733712,5-Dichlorobenzeneboronic acid

생성물 1

HCID 865945994-Chloro-6-(2,5-dichloro-phenyl)-pyrimidin-2-yl-amine수율 31.5%

시약·촉매·용매 3

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

실험 절차

To a mixture of 4,6-dichloro-pyrimidin-2-yl-amine (0.625 g, 3.81 mmol), 2,5-dichloro-phenyl boronic acid (0.726 g, 3.81 mmol), palladium (II) acetate (0.128 g, 0.57 mmol) and triphenylphosphine (0.30 g, 1.14 mmol) was added a solution of sodium carbonate (2.0 g, 19.0 mmol) in water (5 ml) followed by glyme (20 ml). The mixture was stirred under an argon atmosphere for 6 hours. Filtration and concentration of the filtrate yielded the crude product which was purified by flash chromatography on silica gel eluting with ethyl acetate-chloroform (1:8). After evaporation of solvents under reduced pressure, the residue was dissolved in ethanol (100 ml) and stirred while a solution of hydrogen chloride in dioxane (4.0 M, 2.5 ml) was added. After evaporation of volatiles under reduced pressure, the residue was treated with ethyl acetate (25 ml) and stirred for 16 hours. Filtration provided the hydrochloride salt of 4-chloro-6-(2,5-dichloro-phenyl)-pyrimidin-2-yl-amine (0.330 g, 28% yield) as a white powder.

후처리

  1. filtrationFiltration and concentration of the filtrate
  2. customyielded the crude product which
  3. customwas purified by flash chromatography on silica gel eluting with ethyl acetate-chloroform (1:8)
  4. customAfter evaporation of solvents under reduced pressure
  5. dissolutionthe residue was dissolved in ethanol (100 ml)
  6. stirringstirred while a solution of hydrogen chloride in dioxane (4.0 M, 2.5 ml)
  7. additionwas added
  8. customAfter evaporation of volatiles under reduced pressure
  9. additionthe residue was treated with ethyl acetate (25 ml)
  10. stirringstirred for 16 hours
  11. filtrationFiltration

출처 및 근거

ORD 기록
ord-2531632c8b87439aa6a3f8e3c1770705
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419984B2

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