Tributylstannane → HCID 178441857, Verbindung

HRID 486492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 486492
[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10](I)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4].C([SnH](CCCC)CCCC)CCC.[O:30]1CCC[CH2:31]1>CN(C)C=O.C1(C)C=CC=CC=1.[Cl-].[Na+].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>[CH2:1]([C:5]1[NH:6][C:7]2[C:12]([C:13](=[O:15])[N:14]=1)=[CH:11][C:10]([CH:31]=[O:30])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH3:4]

Komponenten

8

Edukt 3

HCID 5948TributylstannaneHCID 8028TetrahydrofuranHCID 178441862HCID 178441862, Verbindung

Produkt 1

HCID 178441857HCID 178441857, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 1.0 g of 2-butyl-6-iodo-4(1H)-quinazolinone and 0.355 g of tetrakis(triphenylphosphine)palladium in 15 ml of tetrahydrofuran and 5 ml of N,N-dimethylformamide, heated to 55° C. under an atmosphere of carbon monoxide is added a solution of 1.40 g of tri-n-butyltin hydride in 2.5 ml of toluene over 6 hours via a syringe pump. After the addition is complete the reaction is allowed to cool to room temperature, diluted with brine and extracted with chloroform. The combined organics are concentrated in vacuo and the resulting residue triturated with ether. The precipitate is collected by filtration and purified by flash chromatography on silica gel, eluting with 1:1 ethyl acetate-hexanes to give 0.35 g of the desired product, m.p. 242°-244° C.

Aufarbeitung

  1. additionAfter the addition
  2. extractionextracted with chloroform
  3. concentrationThe combined organics are concentrated in vacuo
  4. customthe resulting residue triturated with ether
  5. filtrationThe precipitate is collected by filtration
  6. custompurified by flash chromatography on silica gel
  7. washeluting with 1:1 ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-585d6c5062cd41578712e838c3b6d667
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05292734

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