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1-Bromopropane → N,N-Dipropyl-2,5-dimethyl-3-(2,4,6-trimethylphenyl)-2H-pyrazolo[4,3-d]pyrimidin-7-amine

HRID 1155
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1155
[CH2:1]([NH:4][C:5]1[C:6]2[C:7](=[C:12]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=3[CH3:24])[N:13]([CH3:15])[N:14]=2)[N:8]=[C:9]([CH3:11])[N:10]=1)[CH2:2][CH3:3].[OH-].[K+].Br[CH2:28][CH2:29][CH3:30]>CS(C)=O>[CH2:1]([N:4]([CH2:28][CH2:29][CH3:30])[C:5]1[C:6]2[C:7](=[C:12]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=3[CH3:24])[N:13]([CH3:15])[N:14]=2)[N:8]=[C:9]([CH3:11])[N:10]=1)[CH2:2][CH3:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 78401-BromopropaneHCID 14797Potassium HydroxideHCID 15516669N-Propyl-2,5-dimethyl-3-(2,4,6-trimethylphenyl)-2H-pyrazolo[4,3-d]pyrimidin-7-amine

Produkt 1

HCID 9885480N,N-Dipropyl-2,5-dimethyl-3-(2,4,6-trimethylphenyl)-2H-pyrazolo[4,3-d]pyrimidin-7-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl Sulfoxide
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of the product of step F (400 mg, 1.2 mmol), powder KOH (1.0 g) and 1-bromopropane (1 mL) in 2 mL of DMSO was heated at 60° C. for 8 hours. The excess bromopropane was then evaporated. The mixture was partitioned between water and ether. The aqueous layer was separated and extracted with ether. The combined ether extracts were washed with water and brine, dried over Na2SO4 and concentrated to an oil. The oil was purified through silica gel column chromatography to give 260 mg of the title compound as an oil. 1H NMR (CDCl3): d 0.97 (t, 6H), 1.76 (m, 4H), 1.96 (s, 6H), 2.32 (s, 3H), 2.45 (s, 3H), 3.77 (s, 3H), 3.40-4.30 (br, 4H), 6.95 (s, 2H)ppm. The hydrochloride salt prepared in Ether/HCl melted at 210°-13° C.

Aufarbeitung

  1. customThe excess bromopropane was then evaporated
  2. customThe mixture was partitioned between water and ether
  3. customThe aqueous layer was separated
  4. extractionextracted with ether
  5. washThe combined ether extracts were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to an oil
  8. customThe oil was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c0a66d17f4434d27b82b139747ba9e7b
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05723608

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