N-methyl-2-pyrrolidone → HCID 86594941, Verbindung

HRID 969294

Reaktionsgleichung

Reaktionsgleichung von HRID 969294
ClC1C(CCCl)=CN=C([NH:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])N=1.[CH2:21]([CH:24]([NH2:28])[CH2:25][CH2:26][CH3:27])[CH2:22][CH3:23].[CH2:29]([CH:31]([NH2:35])[CH2:32][CH2:33][CH3:34])C.[CH3:36][N:37]1CCC[C:38]1=O>>[CH3:29][C:31]1[C:32]2[CH2:33][CH2:34][N:28]([CH:24]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:22][CH3:23])[C:36]=2[N:37]=[C:38]([C:15]2([CH3:19])[CH:14]=[C:13]([CH3:20])[C:12]([NH2:11])=[C:17]([CH3:18])[CH2:16]2)[N:35]=1

Komponenten

5

Edukt 4

HCID 13387N-methyl-2-pyrrolidoneHCID 386654-HeptanamineHCID 86062Hexan-3-amineHCID 86594942HCID 86594942, Verbindung

Produkt 1

HCID 86594941HCID 86594941, VerbindungAusbeute 41 %

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A solution of [4-chloro-5-(2-chloro-ethyl)-pyrimidin-2-yl]-(2,4,6-trimethyl-phenyl)-amine (1.3 g, 4.1 mmol) in N-methylpyrrolidinone (15 mL) was treated with 1-propyl-butylamine (1.6 g, 14 mmol) and heated to 120° C. in a sealed tube for 18 hours. Additional 1-ethyl-butylamine (0.76 g, 6.6 mmol) was added, and heating at 120° C. was resumed for 32 hours. The reaction mixture was concentrated under reduced pressure and the resulting orange solid was partitioned between ethyl acetate (100 mL) and water (100 mL). The aqueous layer was further extracted with ethyl acetate (2×75 mL), and the combined extracts were washed with 15% aqueous sodium hydroxide (2×50 mL) and brine (30 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude brown oil was chromatographed over silica gel, eluting with a gradient of 1 to 15% methanol in dichloromethane, to provide VII as an off-white solid (0.64 g, 41%; ESIMS m/z (M+H)=367).

Aufarbeitung

  1. temperatureheating at 120° C.
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe resulting orange solid was partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. extractionThe aqueous layer was further extracted with ethyl acetate (2×75 mL)
  5. washthe combined extracts were washed with 15% aqueous sodium hydroxide (2×50 mL) and brine (30 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude brown oil was chromatographed over silica gel
  10. washeluting with a gradient of 1 to 15% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-893813ca57c548cca7e0ec165b7e0013
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07307082B2

Verknüpfte Notizen

Wird geladen…