Potassium Carbonate → (S)-5-Methyl-2-(1-((6-methylthieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1052700
Br[C:2]1[S:30][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][C@H:11]([C:13]3[N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:17](=[O:25])[C:16]4=[C:26]([CH3:29])[CH:27]=[CH:28][N:15]4[N:14]=3)[CH3:12])[C:4]=2[CH:3]=1.[C:31](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.[Cl-].[NH4+]>CN(C)C=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>[CH3:29][C:26]1[CH:27]=[CH:28][N:15]2[C:16]=1[C:17](=[O:25])[N:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]([C@@H:11]([NH:10][C:9]1[C:4]3[CH:3]=[C:2]([CH3:31])[S:30][C:5]=3[N:6]=[CH:7][N:8]=1)[CH3:12])=[N:14]2

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 574072TrimethylboroxineHCID 118433746(S)-2-(1-((6-Bromothieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Produkt 1

HCID 73776064(S)-5-Methyl-2-(1-((6-methylthieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

(S)-2-(1-((6-Bromothieno[2,3-d]pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (50 mg, 0.10 mmol) was dissolved in 3 mL dimethylformamide. Potassium carbonate (287 mg, 2.08 mmol), tetrakis(triphenylphosphine)palladium(0) (12 mg, 0.01 mmol) and trimethylboroxine (130 μl, 0.93 mmol) were added under argon conditions. The reaction mixture was stirred at 130° C. for 2 h. The crude was poured into 25 mL saturated ammonium chloride solution and extracted twice with ethyl acetate. The organics were dried over magnesium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1® Purification System by reverse phase to obtain 26 mg (60% yield) of a yellow solid as a title compound. Purity 100%.

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe organics were dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified
  6. customSP1® Purification System by reverse phase

Quellen und Nachweise

ORD-Eintrag
ord-50ef15b0677243fd9ca87d6588badaa6
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388189B2

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