Butylethylamine → [[6-(Butyl-N-ethylamino)-2-methylpyrimidin-4-yl]-(2,4,6-trimethylphenyl)-amino]-acetic acid ethyl ester

HRID 967953

Reaktionsgleichung

Reaktionsgleichung von HRID 967953
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][N:6]([C:16]1[CH:21]=[C:20](Cl)[N:19]=[C:18]([CH3:23])[N:17]=1)[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=1[CH3:15])[CH3:2].[CH2:25]([NH:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28]>CS(C)=O>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][N:6]([C:16]1[CH:21]=[C:20]([N:29]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:30][CH3:31])[N:19]=[C:18]([CH3:23])[N:17]=1)[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=1[CH3:15])[CH3:2]

Komponenten

4

Edukt 2

HCID 25914Butylethylamine2×HCID 86596480[(6-Chloro-2-methyl-pyrimidin-4-yl)(2,4,6-trimethylphenyl)-amino]-acetic acid ethyl ester

Produkt 1

HCID 69587593[[6-(Butyl-N-ethylamino)-2-methylpyrimidin-4-yl]-(2,4,6-trimethylphenyl)-amino]-acetic acid ethyl esterAusbeute 122,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

A mixture of [(6-chloro-2-methylpyrimidin-4-yl)-(2,4,6-trimethylphenyl)-amino]-acetic acid ethyl ester (85 mg, 0.244 mmol) and N-butyl-ethylamine (0.17 ml, 1.1 mmol) in 4 ml DMSO was heated at 135° C. for 15 hours. An additional 1 ml of N-butyl-ethylamine was added and the reaction was heated at that temperature for an additional 15 hours (tlc showed no starting material). The mixture was quenched with water and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give 123 mg of a light amber oil. The oil was purified through silica gel chromatotron using 5% ethyl acetate in hexane as eluent to give 92 mg (91%) of the title compound as a white glass. 1H NMR (CDCl3) δ 6.94 (s, 2H), 4.69 (s, 1H), 4.23 (s, 2H), 4.22 (q, 2H), 3.35 (q, 2H), 3.15 (t, 2H), 2.36 (s, 3H), 2.31 (s, 3H), 2.21 (s, 6H), 1.3-1.5 (m, 2H), 1.34 (t, 3H), 1.1-1.3 (m, 2H), 1.01 (t, 3H), 0.80 (t, 3H) ppm.

Aufarbeitung

  1. temperaturethe reaction was heated at that temperature for an additional 15 hours (tlc
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6c96099ba8ba48d9991314adf8fd2129
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956047B1

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