Diisopropylethylamine → Ethyl [4-({butyl[5-methyl-6-(4-methylphenyl)pyrimidin-4-yl]amino}methyl)-2-ethylphenoxy]acetate

HRID 1269668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269668
[CH2:1]([NH:5][CH2:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]([CH2:20][CH3:21])[CH:8]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)C(C)C)(C)C.Cl[C:32]1[C:37]([CH3:38])=[C:36]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)[N:35]=[CH:34][N:33]=1>C(Cl)Cl>[CH2:1]([N:5]([CH2:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]([CH2:20][CH3:21])[CH:8]=1)[C:32]1[C:37]([CH3:38])=[C:36]([C:39]2[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=2)[N:35]=[CH:34][N:33]=1)[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 184484024-Chloro-5-methyl-6-(4-methylphenyl)pyrimidineHCID 58622897Ethyl {4-[(butylamino)methyl]-2-ethylphenoxy}acetate

Produkt 1

HCID 58622843Ethyl [4-({butyl[5-methyl-6-(4-methylphenyl)pyrimidin-4-yl]amino}methyl)-2-ethylphenoxy]acetateAusbeute 18,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of ethyl {4-[(butylamino)methyl]-2-ethylphenoxy}acetate (0.23 g, 0.78 mmol), N,N-diisopropylethylamine (0.18 mL, 1.05 mmol) and 4-chloro-5-methyl-6-(4-methylphenyl)pyrimidine (0.114 g, 0.52 mmol) were heated at 100° C. in a sealed reactivial for 18 h. After this time the reactivial was allowed to cool to room temperature and the residue dissolved in CH2Cl2 (50 mL) and washed with water (10 mL) and brine (10 mL). The organic extract was separated by hydrophobic frit and evaporated. Purification by Biotage™ chromatography (Silica, 40 g) eluting 9:1 cyclohexane:EtOAc afforded the title compound as a pale yellow oil (46 mg).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. washwashed with water (10 mL) and brine (10 mL)
  3. extractionThe organic extract
  4. customwas separated by hydrophobic frit
  5. customevaporated
  6. customPurification by Biotage™ chromatography (Silica, 40 g)
  7. washeluting 9:1 cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-56677ac0fd02454c999dd14387ff9aea
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199239B2

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