Water → 2,6-Dimethyl-4-(5-pyrimidinyl)phenol

HRID 63371

반응식

HRID 63371 반응식
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[N:11]1[CH:16]=[C:15](B(O)O)[CH:14]=[N:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:8][C:6]1[CH:7]=[C:2]([C:15]2[CH:16]=[N:11][CH:12]=[N:13][CH:14]=2)[CH:3]=[C:4]([CH3:10])[C:5]=1[OH:9]

참가 물질

7

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 169194-Bromo-2,6-dimethylphenolHCID 2795193(Pyrimidin-5-yl)boronic acid

생성물 1

HCID 683349172,6-Dimethyl-4-(5-pyrimidinyl)phenol수율 20%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 18180031Water 1,2-dimethoxyethane용매

실험 절차

4-Bromo-2,6-dimethylphenol (0.5 g, 2.5 mmol) was dissolved in dimethoxyethane/water (2:1). pyrimidin-5-ylboronic acid (0.37 g, 2.8 mmol), Pd(dppf)Cl2 (0.02 g, 0.13 mmol) and sodium carbonate (0.79 g, 7.5 mmol) were added thereto, followed by reacting in microwave reactor at 120° C. for 15 minutes. After the completion of the reaction, the reaction mixture was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain 2,6-dimethyl-4-(pyrimidin-5-yl)phenol (0.1 g, 20%).

후처리

  1. customAfter the completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe obtained organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-34c8f6cb4a13436397cfcea4147ae4c2
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447083B2

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