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

HRID 275331Notes

Reaction equation

HRID 275331 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f928af98490e40b0831fcfb9f019df66
Source dataset
uspto-grants-1995_02
Patent number
US05393755

Reaction notes

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