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

HRID 1970880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1970880
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-89e230f9231347cba7d7ab8110e549ea
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431572B2

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