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Sodium Carbonate → 5-Biphenyl-4-yl-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine

HRID 19607
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 19607
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([S:14][CH3:15])[N:11]3[N:16]=[CH:17][CH:18]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:2]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([S:14][CH3:15])[N:11]3[N:16]=[CH:17][CH:18]=[C:10]3[CH:9]=2)=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic Acid2×HCID 673194195-(4-Iodo-phenyl)-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine2×

Produkt 1

HCID 673186175-Biphenyl-4-yl-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidineAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 80711,2-DimethoxyethaneLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under an inert gas atmosphere is dissolved 5-(4-iodo-phenyl)-7-methylsulfanyl-pyrazolo[1,5-c]pyrimidine (compound D1)(0.45 g) and phenylboronic acid (0.35 g) in dimethoxyethane. To this solution are added bis-(triphenylphosphine)-palladium(II) chloride (0.19 mmol) and an aqueous sodium carbonate solution (2M, 6 ml). The reaction mixture is heated to reflux for 4.5 h. After 1 h further phenylboronic acid (0.2 g) is added in order to complete the reaction. The mixture is diluted with ethyl acetate and filtered over silica gel. The product is partitioned between ethyl acetate and an aqueous solution of sodium bicarbonate (5%), the organic phase is dried over sodium sulfate and the crude product is purified by silica gel flash chromatography. A nearly colorless solid (0.3 g) in 50% yield is obtained.

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 4.5 h
  3. customthe reaction
  4. filtrationfiltered over silica gel
  5. customThe product is partitioned between ethyl acetate
  6. dry with materialan aqueous solution of sodium bicarbonate (5%), the organic phase is dried over sodium sulfate
  7. customthe crude product is purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-70998479748949489811774a11e6c067
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07745446B2

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