Methyl iodide → HCID 69067168, Verbindung

HRID 1436886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436886
[O:1]=[C:2]([NH:8][CH2:9][C:10]1[N:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].I[CH3:17].[H-].[Na+]>CN(C=O)C>[O:1]=[C:2]([N:8]([CH3:17])[CH2:9][C:10]1[N:11]=[CH:12][CH:13]=[CH:14][N:15]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69066482Ethyl 2-oxo-2-[(pyrimidin-2-yl)methylamino]acetate

Produkt 1

HCID 69067168HCID 69067168, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution ethyl 2-oxo-2-[(pyrimidin-2-yl)methylamino]acetate from the previous step (1.0 g, 4.8 mmol) and iodomethane (0.5 mL, 8 mmol) in DMF (15 mL) was cooled to 0° C. and NaH (0.23 g of a 60% dispersion in mineral oil, 5.7 mmol) was added. The cooling bath was removed and the mixture was stirred at ambient temperature for 18 hours. Ethanol was added to quench the reaction and the solvent was removed under reduced pressure. The residue was purified by pressurized silica gel column chromatography using a gradient of 80-100% EtOAc in hexanes. The solvent was removed under reduced pressure from the fractions containing product to give the title compound as an oil. 1H NMR (400 MHz, DMSO-d6) δ 8.81 (m, 2H), 7.45 (m, 1H), 4.74 (m, 2H), 4.32, 4.13 (two q, rotamers, J=7 Hz, 2H), 3.08, 3.00 (two s, rotamers, 3H), 1.30, 1.08 (two t, rotamers, 3H); ES MS M+1=224.

Aufarbeitung

  1. customThe cooling bath was removed
  2. additionEthanol was added
  3. customto quench
  4. customthe reaction
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by pressurized silica gel column chromatography
  7. customThe solvent was removed under reduced pressure from the fractions
  8. additioncontaining product

Quellen und Nachweise

ORD-Eintrag
ord-c2acfbc5bdca469eb7c5b004ab577b52
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07619086B2

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