Cesium carbonate → 5-(4-Bromophenyl)pyrimidin-2-amine

HRID 1038011Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038011
Br[C:2]1[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO.O.CCOC(C)=O.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:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=2)=[CH:12][CH:11]=1

Komponenten

8

Edukt 3

HCID 10796Cesium carbonateHCID 79599(4-Bromophenyl)boronic acidHCID 2313102-Amino-5-bromopyrimidine

Produkt 1

HCID 595113755-(4-Bromophenyl)pyrimidin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 22242641Methanol--water (1/1)Lösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-pyrimidin-2-ylamine (0.8 g, 4.59 mmol), 4-bromophenyl boronic acid (1 g, 4.97 mmol), tetrakis(triphenylphosphine)palladium(0) (300 mg, 0.259 mmol), cesium carbonate (1.15 g, 3.03 mmol) was stirred in MeOH/H2O (20 ml, 1/1) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200 ml) and water (50 ml). The organic layer was separated, dried over MgSO4, filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 85% v/v EtOAc/hexanes yielding product 81 as white solid. (0.7 g, 63%). ESMS (MH, 250).

Aufarbeitung

  1. temperatureat reflux temperature overnight
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customyielding a residue which
  7. customwas purified on silica gel eluting with 85% v/v EtOAc/hexanes yielding product 81 as white solid

Quellen und Nachweise

ORD-Eintrag
ord-bfa8f93dd33b4e4bab9184efd68cb4e2
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546404B2

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