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

HRID 1175591
Notes
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Reaction equation

HRID 1175591 reaction equation
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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 80711,2-DimethoxyethaneSolvent
HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b0374616427546a294036c938abf74aa
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842324B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes