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

HRID 63371
Notes
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Reaction equation

HRID 63371 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-34c8f6cb4a13436397cfcea4147ae4c2
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447083B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes