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Allyl bromide → 1,6-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-1-(2-propenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester

HRID 1788752
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1788752
[CH3:1][O:2][C:3]1[NH:4][C:5]([CH3:24])=[C:6]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[CH:32]=[CH2:33]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[N:4]([CH2:33][CH:32]=[CH2:31])[CH:5]([CH3:24])[C:6]([C:18]([O:20][CH:21]([CH3:22])[CH3:23])=[O:19])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:8]=1
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Komponenten

6

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 146271971,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methyethyl ester

Produkt 1

HCID 571142891,6-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-1-(2-propenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl esterAusbeute 58,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester (4.0 g, 12.0 mmol; see Example 1A) in dry dimethylformamide (10 ml) was treated with finely ground potassium carbonate (6.6 g, 48.0 mmoles) and allyl bromide (1.7 ml, 20.0 mmole). The resulting suspension was allowed to stir under argon at room temperature for 10 hours. The reaction was diluted with ethyl acetate, filtered and the filtrate was washed with water and brine. It was dried over anhydrous magnesium sulfate and evaporated to provide a yellow oil. Purification by flash chromatography (20% ethyl acetate in hexanes) yielded the title compound (2.64 g) as a yellow oil.

Aufarbeitung

  1. filtrationfiltered
  2. washthe filtrate was washed with water and brine
  3. dry with materialIt was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customto provide a yellow oil
  6. customPurification by flash chromatography (20% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-149ebce89605495e8a96c6b0c1e5b343
Quelldatensatz
uspto-grants-1987_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04684655

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