Pyrimidine → 4-(Tributylstannyl)pyrimidine

HRID 1359283Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359283
C([Li])CCC.CC1(C)CCCC(C)(C)N1.[N:16]1[CH:21]=[CH:20][CH:19]=[N:18][CH:17]=1.[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25]>O.O1CCCC1.CCCCCC>[N:16]1[CH:21]=[CH:20][C:19]([Sn:26]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][CH2:24][CH3:25])=[N:18][CH:17]=1

Komponenten

8

Edukt 4

HCID 9260PyrimidineHCID 130352,2,6,6-TetramethylpiperidineHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Produkt 1

HCID 178300604-(Tributylstannyl)pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5.8 ml of a hexane solution containing 2.52 mol of n-butyllithium was slowly added dropwise into a solution of 20 ml of tetrahydrofuran containing 2.5 ml of 2,2,6,6-tetramethylpiperidine. After stirring at 0° C. for 30 minutes, a mixture of 0.98 ml of pyrimidine, 4.6 ml of tri-n-butyltin chloride and 20 ml of tetrahydrofuran was slowly added dropwise thereinto. After stirring at −78° C. for 4 hours, water was added to the reaction solution and then extracted with ethyl acetate. The organic phase was washed with brine and the solvent was removed. Then, the residue was subjected to silica gel column chromatography to elute with hexane/ethyl acetate (10:1), to give 474 mg of the target compound.

Aufarbeitung

  1. additionwas slowly added dropwise
  2. stirringAfter stirring at −78° C. for 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. customthe solvent was removed
  6. washto elute with hexane/ethyl acetate (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-8546d8822e6c42818a7233f527c31070
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599917B1

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