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Carbamimidic acid, methyl ester, sulfate (1:1) → 1,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester

HRID 1789577
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1789577
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:17](=O)[CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].S(O)(O)(=O)=O.[CH3:25][O:26][C:27](=[NH:29])[NH2:28].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:25][O:26][C:27]1[NH:29][C:17]([CH3:18])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:28]=1
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Komponenten

6

Edukt 3

HCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 367507Ethyl 2-(3-nitrobenzylidene)-3-oxobutanoateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 139125831,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl esterAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A reaction mixture containing 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid, ethyl ester (2.62 g, 10.0 mmole), 2-methylpseudourea sulfate (1.72 g, 10.0 mmole), and sodium bicarbonate (2.52 g, 30.0 mmole) in dimethylformamide (10 ml) was heated at 65°-70° C. for 16 hours. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate, and filtered. The filtrate was washed with water and brine, and then dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a yellow oil which was purified by flash chromatography (5% ethyl acetate in dichloromethane). The resulting foam was crystallized from isopropyl ether/hexanes to provide 2.41 g of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester as a colorless crystalline product; melting point 103.5°-105° C. TLC (silica gel; ethyl acetate: hexanes 50:50) Rf =0.31

Aufarbeitung

  1. temperaturewas heated at 65°-70° C. for 16 hours
  2. filtrationfiltered
  3. washThe filtrate was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave a yellow oil which
  7. customwas purified by flash chromatography (5% ethyl acetate in dichloromethane)
  8. customThe resulting foam was crystallized from isopropyl ether/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-0a3b14c7b922485e955378c7884aefb2
Quelldatensatz
uspto-grants-1987_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04689414

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