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Water → 2-Methyl-2-(4-(pyrimidin-5-yl)phenyl)propanoic acid

HRID 1175591
ノート
印刷プレビュー

反応式

HRID 1175591 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.O.[N:15]1[CH:20]=[C:19](B(O)O)[CH:18]=[N:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.[OH-].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:19]2[CH:20]=[N:15][CH:16]=[N:17][CH:18]=2)=[CH:3][CH:4]=1)([CH3:13])[C:9]([OH:11])=[O:10]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 109336792-(4-Bromophenyl)-2-methylpropanoic acid

生成物 1

HCID 687772492-Methyl-2-(4-(pyrimidin-5-yl)phenyl)propanoic acid収率 74%

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 80711,2-Dimethoxyethane溶媒
HCID 14798Sodium Hydroxide溶媒

反応条件

温度
80 °C

実験手順

2-(4-Bromophenyl)-2-methylpropanoic acid (5.71 g, 23.5 mmol) was dissolved in DME (140 mL) and water (35 mL) and pyrimidin-5-ylboronic acid (2.92 g, 23.5 mmol) and potassium carbonate (11.4 g, 82.2 mmol) were added to the solution. The mixture was degassed using an argon stream, and Pd(PPh3)4 (1.35 g, 1.17 mmol) was added. The mixture was heated (80° C.) under argon overnight then cooled to room temperature. The solution was diluted with 1M NaOH (20 mL) and washed with EtOAc. The aqueous phase was acidified with 6N aq. HCl to pH 4-5 and extracted with EtOAc (3×). The combined extract was successively washed with water and brine, dried over MgSO4, filtered and evaporated to yield 4.2 g (74%) of the crude 2-Methyl-2-(4-(pyrimidin-5-yl)phenyl)propanoic acid (MS+H, 243) that was used in the next step without further purification.

後処理

  1. customThe mixture was degassed
  2. additionwas added
  3. temperaturethen cooled to room temperature
  4. washwashed with EtOAc
  5. extractionextracted with EtOAc (3×)
  6. extractionThe combined extract
  7. washwas successively washed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated

出典と根拠

ORDレコード
ord-b0374616427546a294036c938abf74aa
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07842324B2

反応ノート

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