Tetrahydrofuran → HCID 57747428, Verbindung

HRID 222087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222087
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9][C:10]2[C:11]3[N:34]([CH3:35])[CH:33]=[CH:32][C:12]=3[N:13]=[C:14]([N:16]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[N:15]=2)=[C:4]([CH3:36])[CH:3]=1.[N:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1.C1COCC1.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=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>[CH3:36][C:4]1[CH:3]=[C:2]([C:40]2[CH:41]=[CH:42][N:37]=[CH:38][CH:39]=2)[CH:7]=[C:6]([CH3:8])[C:5]=1[S:9][C:10]1[C:11]2[N:34]([CH3:35])[CH:33]=[CH:32][C:12]=2[N:13]=[C:14]([N:16]([C:24]2[CH:25]=[CH:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=2)[C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[N:15]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 57747383HCID 57747383, Verbindung

Produkt 1

HCID 57747428HCID 57747428, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

tert-Butyl 4-(4-bromo-2,6-dimethylphenylthio)-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-2-yl(4-cyanophenyl)carbamate (0.729 mmol) is combined with pyridine-4-boronic acid (1.46 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.0729 mmol) in a two dram vial. The vial is sealed and flushed with argon. Degassed THF (5.0 mL) and aqueous Na2CO3 (2 M, 1.5 mL, 3.0 mmol) are injected, and the mixture agitated on a shaker at 80° C. for 10 h. The mixture is diluted with ethyl acetate and extracted with aqueous Na2CO3 (0.5 M, ×2). The organic layer is collected, concentrated, and the residue purified by chromatography (SiO2, 1:4 hexanes/EtOAc).

Aufarbeitung

  1. customThe vial is sealed
  2. customflushed with argon
  3. extractionextracted with aqueous Na2CO3 (0.5 M, ×2)
  4. customThe organic layer is collected
  5. concentrationconcentrated
  6. customthe residue purified by chromatography (SiO2, 1:4 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-186c07296949493b96c3766341f57f71
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207178B2

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