N-methyl-2-pyrrolidone → [2,5-Dimethyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-ethyl-propyl-amine

HRID 2183539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2183539
Cl[C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[C:6]2[N:5]=[C:4]([CH3:20])[CH:3]=1.[CH2:21]([NH:24][CH2:25][CH3:26])[CH2:22][CH3:23].[CH3:27]N1CCCC1=O>>[CH3:27][C:9]1[C:10]([C:11]2[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=2[CH3:19])=[C:6]2[N:5]=[C:4]([CH3:20])[CH:3]=[C:2]([N:24]([CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])[N:7]2[N:8]=1

Komponenten

4

Edukt 3

HCID 13387N-methyl-2-pyrrolidoneHCID 883981-Propanamine, N-ethyl-HCID 224743217-Chloro-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 10269356[2,5-Dimethyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidin-7-yl]-ethyl-propyl-amine

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

A mixture of 7-chloro-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (200 mg, 0.66 mmol) and N-propylethylamine (2 ml) in 1 ml of N-methylpyrrolidinone was heated at 135° C. oil bath for 4 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated and purified through silica gel column chromatography using hexane to 10% ethyl acetate in hexane as eluent to give 150 mg of the title compound as a clear green oil. 1H NMR (CDCl3) ä 6.95(s, 2H), 5.80(s, 1H), 3.85(q, 2H), 3.67(dd, 2H), 2.41(s, 3H), 2.32(s, 3H), 2.21(s, 3H), 2.03(s, 6H), 1.76(m, 2H), 1.29(t, 3H), 0.98(t, 3H) ppm.

Aufarbeitung

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. custompurified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8fb6188615d24b16aa40d56765eebe03
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900217B2

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