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Potassium Carbonate → 4-(1-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-phenylamine

HRID 1351162
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1351162
Br[C:2]1[C:10]2[C:5](=[N:6][C:7]([S:11][CH3:12])=[N:8][CH:9]=2)[N:4]([CH3:13])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:28]2[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=2)O1>O1CCOCC1.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>[CH3:13][N:4]1[C:5]2=[N:6][C:7]([S:11][CH3:12])=[N:8][CH:9]=[C:10]2[C:2]([C:28]2[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=2)=[N:3]1
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Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 210980543-bromo-1-methyl-6-(methylsulfanyl)-1H-pyrazolo[3,4-d]pyrimidine

Produkt 1

HCID 210980644-(1-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-phenylamineAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 962WaterLösungsmittel2×
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-1-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine (2.6 g, 10 mmol) in dioxane (40 mL) and H2O (20 mL) was added anhydrous potassium carbonate (4.14 g, 30 mmol, 3 eq), followed by 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (3.28 g, 15 mmol, 1.5 eq). The reaction mixture was degassed and tetrakis(triphenylphosphine)palladium (58 mg, 0.5 mmol, 0.05 eq) was added. The system was then heated under reflux for 24 hours and cooled to room temperature. The mixture was treated with water (150 mL) and cooled to 0° C. and allowed to sit for three hours. The resulting mixture was then filtered. The filtrate was dried in a vacuum oven overnight to afford 1.66 g (61% yield) of 4-(1-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-phenylamine; 1H-NMR (CDCl3): • 2.69 (s, 3H), 3.90 (br s, 2H), 4.08 (s, 3H), 6.82 (d, 2H), 7.77 (d, 2H), 9.11 (s, 1H); LC/MS (m/e)=272.4 (MH+). Rt=1.57 min.

Aufarbeitung

  1. customThe reaction mixture was degassed
  2. temperatureThe system was then heated
  3. temperatureunder reflux for 24 hours
  4. temperaturecooled to 0° C.
  5. filtrationThe resulting mixture was then filtered
  6. customThe filtrate was dried in a vacuum oven overnight

Quellen und Nachweise

ORD-Eintrag
ord-230975ac276c451da880124d48f23985
Quelldatensatz
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07217710B2

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