Potassium Carbonate → FK 360

HRID 255719

Reaktionsgleichung

Reaktionsgleichung von HRID 255719
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23](O)=[O:24].S(Cl)(Cl)=O.[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.CN(C)C=O>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[C:23]([N:34]1[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]1)=[O:24]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 531671-MethylpiperazineHCID 151474876-Methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylic acid

Produkt 1

HCID 3025486FK 360Ausbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylic acid (5 g), dichloromethane (45 ml) and N,N-dimethylformamide (11 ml), thionyl chloride (2.1 g) was added at 7° C. under ice cooling. After stirring for 1.5 hours at the same condition, to a solution of N-methylpiperazine (3.7 g) in dichloromethane (37 ml), the reaction mixture was added under ice cooling and stirred for 2 hours. The reaction mixture was adjusted to pH=8.5 by saturated potassium carbonate and extracted with chloroform. The organic layer was washed with water and brine and dried over magnesium sulfate. The solvent was distilled off to give a residue, which was chromatographed on alumina eluting with a chloroform. The fractions containing the desired product were combined and concentrated in vacuo. The crystalline residue was recrystallized from diethyl ether to afford 6-methyl-5-(4-methylpiperazin-1-ylcarbonyl)-4-(3-nitrophenyl)-2-phenyl-pyrimidine (3.5 g).

Aufarbeitung

  1. additionwas added at 7° C. under ice cooling
  2. additionthe reaction mixture was added under ice cooling
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customto give a residue, which
  8. customwas chromatographed on alumina eluting with a chloroform
  9. additionThe fractions containing the desired product
  10. concentrationconcentrated in vacuo
  11. customThe crystalline residue was recrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-4448fb77d40245da83a2945c0b1bdc5a
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04698340

Verknüpfte Notizen

Wird geladen…