Isopropyl iodide → 6-Bromo-8-isopropyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 2389969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2389969
[H-].[Na+].[Br:3][C:4]1[C:16](=[O:17])[NH:15][C:7]2[N:8]=[C:9]([S:13][CH3:14])[N:10]=[C:11]([CH3:12])[C:6]=2[CH:5]=1.I[CH:19]([CH3:21])[CH3:20]>CN(C=O)C>[Br:3][C:4]1[C:16](=[O:17])[N:15]([CH:19]([CH3:21])[CH3:20])[C:7]2[N:8]=[C:9]([S:13][CH3:14])[N:10]=[C:11]([CH3:12])[C:6]=2[CH:5]=1

Komponenten

5

Edukt 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 592589096-bromo-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Produkt 1

HCID 592589536-Bromo-8-isopropyl-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-oneAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
46 °C

Versuchsvorschrift

To a suspension of NaH (120 mg, 5.00 mmol) in DMF (15 mL) was added 6-bromo-4-methyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (572 mg, 2 mmol). The mixture was heated to 46° C. The solution was cooled down slightly and 2-iodopropane (0.30 mL, 3.0 mmol) was added. The mixture was heated at 46° C. for 30 min and then cooled to room temperature and partitioned between water and ethyl acetate. The organic phase was dried (MgSO4) and concentrated. The crude product was purified by silica gel flash chromatography, using EtOAc/Hexane, to give the title compound (390 mg, 59%).

Aufarbeitung

  1. temperatureThe solution was cooled down slightly
  2. temperatureThe mixture was heated at 46° C. for 30 min
  3. temperaturecooled to room temperature
  4. custompartitioned between water and ethyl acetate
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0742ec46b387422ca53ca4115c308c1c
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273755B2

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