Potassium Phosphate, Tribasic → 2-Chloro-5-cyclopropylpyrimidine

HRID 40564

Reaktionsgleichung

Reaktionsgleichung von HRID 40564
Br[C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:9]1(B(O)O)[CH2:11][CH2:10]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1.O>[Cl:8][C:5]1[N:4]=[CH:3][C:2]([CH:9]2[CH2:11][CH2:10]2)=[CH:7][N:6]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 6066655-Bromo-2-chloropyrimidineHCID 2760897Cyclopropylboronic acid

Produkt 1

HCID 468640872-Chloro-5-cyclopropylpyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3.60 g (18.6 mmol) 5-bromo-2-chloropyrimidine, 4.80 g (55.8 mmol) cyclopropyl boronic acid, 13.8 g (65.1 mmol) K3PO4,568 mg (2.03 mmol) tricyclohexylphosphine and 4 mL water are added to 80 mL toluene. The mixture is degassed thoroughly and charged with 627 mg (2.79 mmol) Pd(OAc)2. After degassing again the mixture is stirred at 100° C. over night, filtered and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, PE/EtOAc 90/10→70/30).

Aufarbeitung

  1. customThe mixture is degassed thoroughly
  2. customAfter degassing again the mixture
  3. filtrationfiltered
  4. customthe solvent is removed in vacuo
  5. customThe crude product is purified by column chromatography (silica gel, PE/EtOAc 90/10→70/30)

Quellen und Nachweise

ORD-Eintrag
ord-61973ad4c4ec4f6fa03b98ec4f2b656c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530460B2

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