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

HRID 63372

反応式

HRID 63372 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

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

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-25183739944245768959d0db5a00b4d8
出典データセット
uspto-grants-2016_09
特許番号
US09447083B2

関連ノート

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