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Sodium Carbonate → N2-{4-[4-amino-1-(1-methyl-3-azetanyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]phenyl}-5,7-dimethyl-1,3-benzoxazol-2-amine

HRID 2056101
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2056101
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH:12]2[CH2:15][N:14]([CH3:16])[CH2:13]2)[N:3]=1.[CH3:17][C:18]1[CH:19]=[C:20]([CH3:43])[C:21]2[O:25][C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30](B4OC(C)(C)C(C)(C)O4)=[CH:29][CH:28]=3)=[N:23][C:22]=2[CH:42]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([CH:12]3[CH2:15][N:14]([CH3:16])[CH2:13]3)[N:3]=[C:2]([C:30]3[CH:29]=[CH:28][C:27]([NH:26][C:24]4[O:25][C:21]5[C:20]([CH3:43])=[CH:19][C:18]([CH3:17])=[CH:42][C:22]=5[N:23]=4)=[CH:32][CH:31]=3)[C:10]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 11581347(5,7-Dimethyl-benzoxazol-2-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-amineHCID 223473823-iodo-1-(1-methyl-3-azetanyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Produkt 1

HCID 22347401N2-{4-[4-amino-1-(1-methyl-3-azetanyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]phenyl}-5,7-dimethyl-1,3-benzoxazol-2-amineAusbeute 57,7 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-iodo-1-(1-methyl-3-azetanyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.17 g, 0.00052 mol), N-(5,7-dimethyl-1,3-benzoxazol-2-yl)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (0.23 g, 0.000624 mol), tetrakis(triphenylphosphine)-palladium (0.030 g, 0.000026 mol) and sodium carbonate (0.14 g, 0.0013 mol) in ethylene glycol dimethyl ether (20 mL) and water (15 mL) was heated at 80° C. for 16 hours under an atmosphere of nitrogen. The reaction was cooled to room temperature. The mixture was allowed to cool to ambient temperature, and the solvent was removed under the reduced pressure. The residue was partitioned between water and dichloromethane. The aqueous layer was extracted with dichloromethane (3×50 mL). The combined organic extracts were washed with water, saturated aqueous sodium bicarbonate solution, and brine, and dried over magnesium sulfate. The solvents were evaporated under the reduced pressure to leave a brownish solid which was purified by flash column chromatography on silica using 5%-50% methanol/dichloromethane as a mobile phase to give N2-{4-[4-amino-1-(1-methyl-3-azetanyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]phenyl}-5,7-dimethyl-1,3-benzoxazol-2-amine (0.13 g, 0.0003 mol).

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. temperatureto cool to ambient temperature
  3. customthe solvent was removed under the reduced pressure
  4. customThe residue was partitioned between water and dichloromethane
  5. extractionThe aqueous layer was extracted with dichloromethane (3×50 mL)
  6. washThe combined organic extracts were washed with water, saturated aqueous sodium bicarbonate solution, and brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvents were evaporated under the reduced pressure
  9. customto leave a brownish solid which
  10. customwas purified by flash column chromatography on silica using 5%-50% methanol/dichloromethane as a mobile phase

Quellen und Nachweise

ORD-Eintrag
ord-3dff4463156c42e0adb9b82cd69f4ecd
Quelldatensatz
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07332497B2

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