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Water → N-butyl-N-ethyl-2,5-dimethyl-7-(2,4,6-trimethylphenyl)pyrrolo(2,3-d)pyrimidin-4-amine

HRID 1884344
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1884344
Cl[C:2]1[C:3]2[C:11]([CH3:12])=[CH:10][N:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[CH2:22]([NH:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH3:23].O>CS(C)=O.Cl>[CH2:25]([N:24]([CH2:22][CH3:23])[C:2]1[C:3]2[C:11]([CH3:12])=[CH:10][N:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1)[CH2:26][CH2:27][CH3:28]
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Komponenten

6

Edukt 3

HCID 962WaterHCID 25914ButylethylamineHCID 107805364-Chloro-7-mesityl-2,5-dimethyl-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 5311055N-butyl-N-ethyl-2,5-dimethyl-7-(2,4,6-trimethylphenyl)pyrrolo(2,3-d)pyrimidin-4-amineAusbeute 81,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidKatalysator
HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-2,5-dimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidine (1.000 g, 3.36 mmol) and N-ethylbutylamine (3.400 g, 33.60 mmol) in 5 ml of dimethylsulfoxide was heated to reflux for 1.5 hours. The mixture was cooled and treated with water and a few drops of 2 N HCl to pH 6.5 and extracted with ethyl acetate. The organic layer was separated, washed with dilute sodium bicarbonate, brine, and dried over sodium sulfate anhydrous and concentrated to dryness. The residue was purified through silica gel column chromatography to give 995 mg (81% yield) of the title compound as an oil. 1H NMR (CDCl3) δ 6 0.90 (t, 3H), 1.23(t, 3H), 1.35(m, 2H), 1.60-1.70(m, 2H), 1.92(s, 6H), 2.30(s, 3H), 2.40(s, 3H), 2.46(s, 3H), 3.58(t, 2H), 3.66(q, 2H), 6.55(s, 1H), 6.95(s, 2H) ppm. The corresponding hydrogen chloride salt was prepared as a white crystals after recrystallization from ethyl acetate. 1H NMR (D2O) δ 0.90(t, 3H), 1.34(m, 5H), 1.75(m, 2H), 1.90(s, 6H), 2.37(s, 3H), 2.48(s, 3H), 2.55(s, 3H), 3.80-3.94(m, 4H), 7.09(s, 2H) ppm.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with dilute sodium bicarbonate, brine
  7. dry with materialdried over sodium sulfate anhydrous
  8. concentrationconcentrated to dryness
  9. customThe residue was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e6d9822e2f094164ac06e033b3a6fe2d
Quelldatensatz
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06765008B1

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