Diisopropylethylamine → Methyl [4-[(2,2-dimethoxyethyl)amino]-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate

HRID 2353323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2353323
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][N:5]=[C:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[N:3]=1.[CH3:23][O:24][CH:25]([O:28][CH3:29])[CH2:26][NH2:27].C(N(CC)C(C)C)(C)C>O1CCOCC1>[CH3:23][O:24][CH:25]([O:28][CH3:29])[CH2:26][NH:27][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][N:5]=[C:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 89728Aminoacetaldehyde dimethyl acetalHCID 57542076Methyl [4-chloro-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate

Produkt 1

HCID 57542083Methyl [4-[(2,2-dimethoxyethyl)amino]-2-(4-nitrobenzyl)pyrimidin-5-yl]acetateAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of methyl [4-chloro-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (2.70 g, 8.39 mmol) and aminoacetoaldehyde dimethyl acetal (1.83 mL, 16.78 mmol) in dioxane (40 mL) was added N,N-diisopropylethylamine (1.46 mL, 8.39 mmol). The mixture was stirred at 85° C. for 1 day. After cooling to room temperature, the reaction was quenched with water, and extracted with ethyl acetate. The extracts were washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica-gel, (ethyl acetate) to give methyl [4-[(2,2-dimethoxyethyl)amino]-2-(4-nitrobenzyl)-pyrimidin-5-yl]acetate (2.41 g, 74%) as brown oil.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography on silica-gel, (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a87927881036477bb026a80bfce37c20
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750014B2

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