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3-Pyridinecarboxaldehyde → 4,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-alpha-(3-pyridinyl)-2-pyrimidine-ethanol

HRID 6343
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 6343
C([Li])CCC.[CH3:6][C:7]([C:10]1[C:15]([O:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:13]=[C:12]([CH3:27])[N:11]=1)([CH3:9])[CH3:8].[N:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH:34]=[O:35])[CH:29]=1>C1COCC1>[CH3:9][C:7]([C:10]1[C:15]([O:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH3:22])=[C:14]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:13]=[C:12]([CH2:27][CH:34]([C:30]2[CH:29]=[N:28][CH:33]=[CH:32][CH:31]=2)[OH:35])[N:11]=1)([CH3:6])[CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 103713-PyridinecarboxaldehydeHCID 199229904,6-Ditert-butyl-5-[(2-methoxyethoxy)methoxy]-2-methylpyrimidineHCID 178418339Butyllithium

Produkt 1

HCID 190071464,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-alpha-(3-pyridinyl)-2-pyrimidine-ethanolAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

n-Butyllithium (1.5 mL of 1.6M solution in hexane, 2.4 mmol) is added dropwise to a solution of 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-2-methylpyrimidine (750 mg, 2.4 mmol) in dry THF (12 mL) at 0° C. under an atmosphere of dry nitrogen. The reaction mixture is stirred at room temperature for 30 minutes and then cooled to -78° C. A solution of pyridine 3-carboxaldehyde (250 mg, 2.4 mmol) in dry THF (1 mL) is added dropwise. The reaction mixture is stirred at room temperature for 3 hours and then is quenched by the addition of saturated aqueous ammonium chloride. The product is extracted into ether. The organic layer is dried (MgSO4) and evaporated to give crude 4,6-bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)methoxy]-α-(3- pyridinyl)- 2-pyrimidineethanol (500 mg, 50%) which is not further purified, but used directly in the next reaction.

Aufarbeitung

  1. temperaturecooled to -78° C
  2. stirringThe reaction mixture is stirred at room temperature for 3 hours
  3. customis quenched by the addition of saturated aqueous ammonium chloride
  4. extractionThe product is extracted into ether
  5. dry with materialThe organic layer is dried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-f8b7c078c1f34c738ce919fd25bc8ca3
Quelldatensatz
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05248682

Notizen zur Reaktion

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