Benzaldehyde → 6-Amino-3-methyl-5-(phenylmethyleneamino)pyrimidine-2,4-dione

HRID 275331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275331
[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[N:11]=O.[OH-].[Na+].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[Pd].O>[NH2:1][C:2]1[NH:7][C:6](=[O:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[N:11]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 32477206-Amino-3-methyl-5-nitroso-1,2,3,4-tetrahydropyrimidine-2,4-dione

Produkt 1

HCID 126359336-Amino-3-methyl-5-(phenylmethyleneamino)pyrimidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

6-amino-3-methyl-5-nitrosopyrimidine-2,4-dione (37.5 g=0.22 mol) with 10% palladium on carbon (Pd/C) (1.9 g) and 25% NaOH (25 ml) in 0.75L water. Hydrogenate at 50 psi for 3 hr, filter through Celite, and dilute to 1.5L with water. Adjust to pH 4.5 with HOAc and add benzaldehyde (35 g=0.34 mol). Add 0.5 kg ice, collect the solid, wash with water, then acetonitrile, and dry to give the title compound as a yellow powder.

Aufarbeitung

  1. filtrationfilter through Celite
  2. additiondilute to 1.5L with water
  3. customcollect the solid
  4. washwash with water
  5. dry with materialacetonitrile, and dry

Quellen und Nachweise

ORD-Eintrag
ord-f928af98490e40b0831fcfb9f019df66
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393755

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