4,6-Bis(1,1-dimethylethyl)-5-hydroxy-N-methoxy-N-methyl-2-pyrimidinecarboxamide → 1-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-1-propanone

HRID 1033759Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1033759
[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([C:16](N(OC)C)=[O:17])[N:6]=1)([CH3:4])[CH3:3].[CH2:22]([Mg]Br)[CH3:23]>O1CCCC1.C(OCC)C>[CH3:13][C:12]([C:9]1[C:10]([OH:11])=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[N:6]=[C:7]([C:16](=[O:17])[CH2:22][CH3:23])[N:8]=1)([CH3:14])[CH3:15]

Komponenten

5

Edukt 2

HCID 100401704,6-Bis(1,1-dimethylethyl)-5-hydroxy-N-methoxy-N-methyl-2-pyrimidinecarboxamideHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 104229331-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-1-propanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 8.4 g (28 mmol) of 4,6-bis(1,1-dimethylethyl)-5-hydroxy-N-methoxy-N-methyl-2-pyrimidinecarboxamide in 150 mL of tetrahydrofuran was cooled in ice and treated dropwise with 40 mL (120 mmol) of a 3.0 M solution of ethylmagnesium bromide in diethyl ether. The mixture was stirred in ice for 2 hours, then at room temperature for an additional 16 hours. The reaction mixture was again cooled in ice, and excess Grignard reagent was destroyed by dropwise addition of 50 mL of saturated aqueous ammonium chloride solution. The reaction mixture was added to 400 mL of ammonium chloride solution and extracted several times with ethyl acetate. The combined organic layers were washed with brine, dried (anhydrous sodium sulfate), and evaporated. Recrystallization of the residue from hexane yielded 5.0 g (67%) of the ethyl ketone product, mp 123° C. -125° C.

Aufarbeitung

  1. waitat room temperature for an additional 16 hours
  2. temperatureThe reaction mixture was again cooled in ice
  3. customexcess Grignard reagent was destroyed by dropwise addition of 50 mL of saturated aqueous ammonium chloride solution
  4. additionThe reaction mixture was added to 400 mL of ammonium chloride solution
  5. extractionextracted several times with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (anhydrous sodium sulfate)
  8. customevaporated
  9. customRecrystallization of the residue from hexane
  10. customyielded 5.0 g (67%) of the ethyl ketone product, mp 123° C. -125° C.

Quellen und Nachweise

ORD-Eintrag
ord-83cb07ac8eed41129e04b9b768fdbedb
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05312821

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