Sodium Carbonate → (3-(5-Bromopyrimidin-2-yl)phenyl)methanol

HRID 2088405Notes

Reaction equation

HRID 2088405 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Br:7][C:8]1[CH:9]=[N:10][C:11](I)=[N:12][CH:13]=1.[OH:15][CH2:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1>O.C1(C)C=CC=CC=1.C(O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:7][C:8]1[CH:9]=[N:10][C:11]([C:21]2[CH:22]=[C:17]([CH2:16][OH:15])[CH:18]=[CH:19][CH:20]=2)=[N:12][CH:13]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 70066515-Bromo-2-iodopyrimidine

Product 1

HCID 59484879(3-(5-Bromopyrimidin-2-yl)phenyl)methanol

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 70.0 g (660 mmol) of sodium carbonate in 325 ml of water is added to a solution, kept under nitrogen, of 95.0 g (332 mmol) of 5-bromo-2-iodopyrimidine in 325 ml of toluene, and the mixture is heated to 80° C. 2.3 g (3.3 mmol) of bis(triphenylphosphine)palladium(II) chloride are added, and a solution of 50.0 g (329 mmol) of 3-(hydroxymethyl)benzeneboronic acid in 650 ml of ethanol is subsequently added dropwise. The reaction mixture is stirred at 80° C. for 18 hours. The reaction mixture is cooled to room temperature and filtered. 1 l of ethyl acetate and 1 l of water are added to the filtrate. The organic phase is separated off, dried over sodium sulfate and evaporated. The residue is recrystallised from 2-propanol: [3-(5-bromopyrimidin-2-yl)-phenyl]methanol as pale-yellow crystals; m.p. 115-116° C.; LCMS 265, 267.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationfiltered
  3. addition1 l of ethyl acetate and 1 l of water are added to the filtrate
  4. customThe organic phase is separated off
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue is recrystallised from 2-propanol

Sources & evidence

ORD record
ord-441f798390c846c0855fbb095fab460d
Source dataset
uspto-grants-2013_05
Patent number
US08435986B2

Reaction notes

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