tert-Butyl methyl ether → (3-(5-Bromopyrimidin-2-yl)phenyl)methanol

HRID 655334Notes

Reaction equation

HRID 655334 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[OH:9][CH2:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.O.O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].COC(C)(C)C>O1CCOCC1.O.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>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:15]2[CH:16]=[C:11]([CH2:10][OH:9])[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 70066515-Bromo-2-iodopyrimidineHCID 18407952Tripotassium phosphate trihydrate

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

750 mg (0.65 mmol) of tetrakis(triphenylphosphine)palladium are added to a solution, kept under nitrogen, of 6.11 g (21.5 mmol) of 5-bromo-2-iodopyrimidine, 3.91 g (25.7 mmol) of 3-(hydroxymethyl)benzeneboronic acid and 9.11 g (42.9 mmol) of tripotassium phosphate trihydrate in 120 ml of dioxane and 14 ml of water, and the mixture is stirred at 90° C. for 18 hours. The reaction mixture is cooled to room temperature, tert-butyl methyl ether and water are added, and the mixture is filtered through kieselguhr. The organic phase of the filtrate is separated off, dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationthe mixture is filtered through kieselguhr
  3. customThe organic phase of the filtrate is separated off
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-345154de3cce443982329c4f7cf98de8
Source dataset
uspto-grants-2011_12
Patent number
US08071593B2

Reaction notes

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