Sodium Carbonate → 6-(4-aminophenyl)-N-[(1S)-1-phenylethyl]pyrazin-2-amine

HRID 1244408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1244408
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH:5]=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[NH2:29][C:28]1[CH:30]=[CH:31][C:25]([C:2]2[N:7]=[C:6]([NH:8][C@H:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH3:10])[CH:5]=[N:4][CH:3]=2)=[CH:26][CH:27]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 587170806-Chloro-N-[(1S)-1-phenylethyl]pyrazin-2-amine

Produkt 1

HCID 587170936-(4-aminophenyl)-N-[(1S)-1-phenylethyl]pyrazin-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 6-chloro-N-[(1S)-1-phenylethyl]pyrazin-2-amine (1.10 g, 4.71 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (1.10 g, 5.02 mmol), (PPh3)4Pd (580 mg, 0.5 mmol) and a Na2CO3 solution (2.6 ml, 2M solution) in toluene (20 ml) was heated under reflux for 40 h. Upon cooling, the mixture was diluted with water (30 mL) and the product extracted with ethyl acetate (3×40 ml). The organic layers were combined, washed with brine (30 ml), dried (Na2SO4), and the solvent removed in vacuo. The residue was purified by column chromatography, eluting with a hexane-ethyl acetate (2:3) to furnish the desired product from the polar fractions (0.86 g, 63%).

Aufarbeitung

  1. temperatureunder reflux for 40 h
  2. temperatureUpon cooling
  3. extractionthe product extracted with ethyl acetate (3×40 ml)
  4. washwashed with brine (30 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluting with a hexane-ethyl acetate (2:3)

Quellen und Nachweise

ORD-Eintrag
ord-6911be29f3504cf2bdba68e191247300
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07122550B2

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