Sodium Carbonate → 4-Chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine

HRID 28569

반응식

HRID 28569 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:12]=[CH:13][C:14]([O:20][CH2:21][CH3:22])=[C:15](B(O)O)[CH:16]=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.CC(C)=O.C(COC)OC>[Cl:8][C:6]1[CH:7]=[C:2]([C:13]2[CH:12]=[C:11]([Cl:10])[CH:16]=[CH:15][C:14]=2[O:20][CH2:21][CH3:22])[N:3]=[C:4]([NH2:9])[N:5]=1

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 655222-Amino-4,6-dichloropyrimidineHCID 37008365-Chloro-2-ethoxyphenylboronic acid

생성물 1

HCID 860043254-Chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine수율 73.3%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 180Acetone용매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a mixture of 4,6-dichloro-pyrimidin-2-ylamine (0.50 g, 3.0 mmol), 5-chloro-2-ethoxy-phenyl boronic acid (0.61 g, 3.0 mmol), palladium (II) acetate (0.10 g, 0.46 mmol), and triphenylphosphine (0.24 g, 0.91 mmol) was added a solution of sodium carbonate (1.6 g, 15.2 mmol) in water (5 ml) followed by glyme (20 ml). The mixture was stirred under an argon atmosphere at room temperature for 3.5 hours. Acetone (20 ml) was added and the mixture was filtered through a pad of celite under suction. The filtrated was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel eluting with 15% ethyl acetate-hexane followed by 20% ethyl acetate-hexane to provide 4-chloro-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-2-ylamine (0.625 g, 73% yield) as a white powder.

후처리

  1. filtrationthe mixture was filtered through a pad of celite under suction
  2. concentrationThe filtrated was concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography on silica gel eluting with 15% ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-582a73f2ba0f47c68b8c414e243374b1
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419984B2

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