Sodium Carbonate → 4-(2-Aminopyrimidin-5-yl)-2-fluorophenol

HRID 500150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500150
Br[C:2]1[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[F:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][C:15]=1[OH:16].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.C1(C)C=CC=CC=1.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>[NH2:8][C:5]1[N:4]=[CH:3][C:2]([C:12]2[CH:13]=[CH:14][C:15]([OH:16])=[C:10]([F:9])[CH:11]=2)=[CH:7][N:6]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 2313102-Amino-5-bromopyrimidineHCID 23005361(3-Fluoro-4-hydroxyphenyl)boronic acid

Produkt 1

HCID 672239574-(2-Aminopyrimidin-5-yl)-2-fluorophenol

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 5-bromopyrimidin-2-amine (3.3 g, 19 mmol), (3-fluoro-4-hydroxyphenyl)boronic acid (2.7 g, 17 mmol), tetrakis(triphenylphosphine)palladium (0.6 g, 0.5 mmol), sodium carbonate (18.3 g, 172 mmol) in ethanol (15 mL), water (5 mL) and toluene (15 mL) was heated at 120° C. for 3 h. The volatiles were removed under reduced pressure. The residue was diluted with EtOAc, washed with water and brine, dried over MgSO4, filtered, and concentrated to obtain the desired product which was directly used in the next step.

Aufarbeitung

  1. customThe volatiles were removed under reduced pressure
  2. additionThe residue was diluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5d3f90848d484d2798809606327f0d7c
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767675B2

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