Ethyl Acetate → 3-[6-(Cyclohexyloxy)pyridin-3-yl]pyrazin-2-amine

HRID 1622689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1622689
Cl[C:2]1[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][N:7]=1.[CH:9]1([O:15][C:16]2[N:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[Na+].[Na+].CCOC(C)=O>COCCOC.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>[CH:9]1([O:15][C:16]2[N:21]=[CH:20][C:19]([C:2]3[C:3]([NH2:8])=[N:4][CH:5]=[CH:6][N:7]=3)=[CH:18][CH:17]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2762242-Amino-3-chloropyrazineHCID 66747855B-[6-(cyclohexyloxy)-3-pyridinyl]Boronic acid

Produkt 1

HCID 667485613-[6-(Cyclohexyloxy)pyridin-3-yl]pyrazin-2-amineAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium(0) (53.5 mg) was added to a suspension of 3-chloropyrazin-2-amine (200 mg), 6-(cyclohexyloxy)pyridin-3-ylboronic acid (375 mg) and sodium carbonate (327 mg) in DME (5 mL) and water (1 mL) and the mixture was stirred at 90° C. under nitrogen for 3 hr. Water and EtOAc were added and the organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane) and washed with IPE to give the title compound (332 mg) as brown gum.

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, eluted with EtOAc in hexane)
  6. washwashed with IPE

Quellen und Nachweise

ORD-Eintrag
ord-3dd1162dd921459f977327b3ac0b5e49
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778934B2

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