3-Pentanol → 4-(1-Ethyl-propoxy)-2,5-dimethyl-7-(2,4,6-trimethyl-phenyl)-5H-pyrrolo[3,2-d]py-rimidine

HRID 2183543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2183543
[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].[H-].[Na+].Cl[C:10]1[C:11]2[N:19]([CH3:20])[CH:18]=[C:17]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])[C:12]=2[N:13]=[C:14]([CH3:16])[N:15]=1>C1COCC1>[CH2:2]([CH:3]([O:6][C:10]1[C:11]2[N:19]([CH3:20])[CH:18]=[C:17]([C:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=3[CH3:29])[C:12]=2[N:13]=[C:14]([CH3:16])[N:15]=1)[CH2:4][CH3:5])[CH3:1]

Komponenten

5

Edukt 3

HCID 114283-PentanolHCID 24758Sodium hydrideHCID 224743134-Chloro-2,5-dimethyl-7-(2,4,6-trimethyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine

Produkt 1

HCID 99030994-(1-Ethyl-propoxy)-2,5-dimethyl-7-(2,4,6-trimethyl-phenyl)-5H-pyrrolo[3,2-d]py-rimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 3-pentanol (0.09 ml, 0.883 mmol) in dry THF was added 60% NaH in oil (20 mg, 0.500 mmol) and stirred for 5 min. A solution of 4-chloro-2,5-dimethyl-7-(2,4,6-trimethyl-phenyl)-5H-pyrrolo[3,2-d]pyrimidine (50 mg, 0.166 mmol) in dry THF was added to the reaction mixture and the resulting mixture was heated at reflux for 2 hr. The mixture was quenched with water, extracted with ethyl acetate. The organic layer was washed with brine, separated, dried and concentrated to dryness to give the title compound as a white solid. 1H NMR (CDCl3) ä 6.92(s, 3H), 5.43(m, 1H), 4.02(s, 3H), 2.56(s, 3H), 2.29(s, 3H), 2.08(s, 6H), 1.80(m, 4H), 0.99(t, 6H).

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 hr
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customseparated
  7. customdried
  8. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-37a2327f738142abac116099ba315b98
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900217B2

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