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Triethylamine → 3-(2,2-Dimethyl-1-oxopropyl)-1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid, ethyl ester

HRID 1590298
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1590298
C[O:2][C:3]1[NH:4][C:5]([CH3:23])=[C:6]([C:18]([O:20][CH2:21][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(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:40](Cl)(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42]>ClCCl>[CH3:42][C:41]([CH3:44])([CH3:43])[C:40]([N:8]1[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]([CH3:23])[NH:4][C:3]1=[O:2])=[O:45]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 62493Pivaloyl chlorideHCID 139125831,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester

Produkt 1

HCID 867467173-(2,2-Dimethyl-1-oxopropyl)-1,2,3,4-tetrahydro-6-methyl-4-(3-nitrophenyl)-2-oxo-5-pyrimidinecarboxylic acid, ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.96 g., 3.0 mmole), dry triethylamine (1.25 ml., 9.0 mmole), and dimethylaminopyridine (36 mg., 0.3 mmole) in dichloromethane (12 ml.) under argon is treated with pivaloyl chloride (0.44 ml., 3.6 mmole). After stirring for 45 minutes at room temperature, the reaction mixture is evaporated. The residue is taken up in tetrahydrofuran/methanol (10 ml. each) and treated with 2N hydrochloric acid (6.0 ml., pH 1). After stirring at room temperature for 3.0 hours, the reaction is quenched with saturated sodium bicarbonate, partially evaporated and extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride and evaporated. Flash chromatography and crystallization from dichloromethane/isopropyl ether gives the title compound as white crystals (420 mg. , m. p. 155°-156°. TLC(silica gel; ethyl acetate:hexane, 1:1)Rf =0.67.

Aufarbeitung

  1. customthe reaction mixture is evaporated
  2. additioneach) and treated with 2N hydrochloric acid (6.0 ml., pH 1)
  3. stirringAfter stirring at room temperature for 3.0 hours
  4. customthe reaction is quenched with saturated sodium bicarbonate
  5. custompartially evaporated
  6. extractionextracted with ethyl acetate
  7. washThe organic phase is washed with saturated sodium chloride
  8. customevaporated
  9. customFlash chromatography and crystallization from dichloromethane/isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-98b2611ecfbf4c4795d62d4917581552
Quelldatensatz
uspto-grants-1993_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05202330

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