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Methyl iodide → 5-(1,1-Dimethylethyl) 4-methyl 6-methyl-4,5-pyrimidinedicarboxylate

HRID 227579
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 227579
[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].IC.[C:20](=O)([O-])[O-].[Li+].[Li+]>CN(C)C=O>[CH3:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH3:20])=[O:9])[C:3]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11125Lithium CarbonateHCID 671825105-(1,1-Dimethylethyl) hydrogen 6-methyl-4,5-pyrimidinedicarboxylate

Produkt 1

HCID 671843365-(1,1-Dimethylethyl) 4-methyl 6-methyl-4,5-pyrimidinedicarboxylateAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 9.12 g (38 mmol) of the material from Step B in 100 mL of N,N-dimethyl formamide (DMF) was added 3.1 mL (50 mmol) of iodomethane and 3.7 g (50 mmol) of lithium carbonate. The reaction mixture was heated at 60° C. for 3 hours. After cooling the reaction mixture was partitioned between dichloromethane and water. The organic layer was dried (sodium sulfate) and the solvent was removed with a rotary evaporator and then a vacuum pump. The residue was purified by MPLC with a gradient of 20-30% ethyl acetate in hexanes as eluant to afford 7.58 g of the title compound as an off-white solid.

Aufarbeitung

  1. temperatureAfter cooling the reaction mixture
  2. customwas partitioned between dichloromethane and water
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. customthe solvent was removed with a rotary evaporator
  5. customThe residue was purified by MPLC with a gradient of 20-30% ethyl acetate in hexanes as eluant

Quellen und Nachweise

ORD-Eintrag
ord-945412e5f1a24566adb2db44b9eadcf2
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560564B2

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