Thiazole → 6-(3-Fluorophenyl)-5-(1,3-thiazol-5-yl)pyrazin-2-amine

HRID 1710693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710693
Br[C:2]1[N:3]=[CH:4][C:5]([NH2:15])=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=1.[S:16]1[CH:20]=[CH:19][N:18]=[CH:17]1.C([O-])(=O)C.[K+]>CN(C)C(=O)C.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>[F:14][C:10]1[CH:9]=[C:8]([C:7]2[N:6]=[C:5]([NH2:15])[CH:4]=[N:3][C:2]=2[C:20]2[S:16][CH:17]=[N:18][CH:19]=2)[CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 3

HCID 9256ThiazoleHCID 517044Potassium AcetateHCID 594576145-Bromo-6-(3-fluorophenyl)pyrazin-2-amine

Produkt 1

HCID 160716586-(3-Fluorophenyl)-5-(1,3-thiazol-5-yl)pyrazin-2-amineAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 5-bromo-6-(3-fluorophenyl)pyrazin-2-amine (Preparation 1, 100 mg, 0.37 mmol), thiazole (0.06 mL, 0.88 mmol) and potassium acetate (54 mg, 0.56 mmol) in N,N-dimethylacetamide (1 mL) was degassed with argon. The catalyst Pd(PPh3)4 (23 mg, 0.02 mmol, 5 mol %) was added and degassing was repeated. The mixture was heated to 150° C. in a sealed tube and stirred overnight. The mixture was cooled and ethyl acetate and aqueous NH4Cl were added. The aqueous layer was extracted with ethyl acetate. The organic layer was dried and concentrated. The residue was purified by flash silica gel chromatography (hexanes/EtOAc 1:1) to give the title compound (15 mg, 15%) as a yellow solid.

Aufarbeitung

  1. customwas degassed with argon
  2. customdegassing
  3. temperatureThe mixture was cooled
  4. additionethyl acetate and aqueous NH4Cl were added
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customThe residue was purified by flash silica gel chromatography (hexanes/EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3b4e63fdc40a4595a055f67b308f0ab7
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790728B2

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