Water → 4-(2-Amino-5-pyrimidinyl)-2,6-dimethylphenol

HRID 63372

Reaction equation

HRID 63372 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5](B(O)O)=[CH:4][N:3]=1.Br[C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([OH:19])=[C:14]([CH3:20])[CH:13]=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]>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([OH:19])=[C:14]([CH3:20])[CH:13]=2)=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 169194-Bromo-2,6-dimethylphenolHCID 17750211(2-Aminopyrimidin-5-yl)boronic acid

Product 1

HCID 900021814-(2-Amino-5-pyrimidinyl)-2,6-dimethylphenolYield 27.8%

Reagents, catalysts & solvents 2

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

Procedure

2-Aminopyrimidin-5-ylboronic acid (0.76 g, 5.4 mmol) was dissolved in dimethoxyethane/water (2:1). 4-Bromo-2,6-dimethylphenol (0.91 g, 4.52 mmol) and Pd(dppf)Cl2 (0.19 g, 0.14 mmol), sodium carbonate (1.4 g, 14 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 dichloromethane. The obtained organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain 4-(2-aminopyrimidin-5-yl)-2,6-dimethylphenol (0.27 g, 27%).

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted with dichloromethane
  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-25183739944245768959d0db5a00b4d8
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Linked notes

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