Cyanoacetic acid → n-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-2-cyanoacetamide

HRID 544737Notes

Reaction equation

HRID 544737 reaction equation
O.[NH2:2][C:3]1[C:4](=[O:13])[N:5]([CH3:12])[C:6](=[O:11])[N:7]([CH3:10])[C:8]=1[NH2:9].[C:14]([CH2:16][C:17](O)=[O:18])#[N:15]>CC(C)=O>[C:14]([CH2:16][C:17]([NH:2][C:3]1[C:4](=[O:13])[N:5]([CH3:12])[C:6](=[O:11])[N:7]([CH3:10])[C:8]=1[NH2:9])=[O:18])#[N:15]

Participants

4

Reactant 2

HCID 9740Cyanoacetic acidHCID 122574835,6-diamino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione hydrate

Product 1

HCID 225212n-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-2-cyanoacetamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5,6-diamino-1,3-dimethyluracil hydrate (19.0 g, 0.11 mole) and cyanoacetic acid (19.0 g, 0.22 mole) is heated to 120°-130° C. under a nitrogen atmosphere. The mixture melts and resolidifies within thirty minutes. The resolidified residue is cooled to room temperature and is taken up in acetone. The residue is collected on a filter, recrystallized in water using decolorizing carbon, dried, and triturated under vacuum to yield 5-cyanoacetamido-6-amino-1,3-dimethyluracil as a solid (14.2 g; 54%).

Workup

  1. temperatureis heated to 120°-130° C. under a nitrogen atmosphere
  2. waitresolidifies within thirty minutes
  3. customThe residue is collected on a filter
  4. customrecrystallized in water using
  5. customdried
  6. customtriturated under vacuum

Sources & evidence

ORD record
ord-8466983398c5404ab67d0471f7b6a07a
Source dataset
uspto-grants-1984_05
Patent number
US04451652

Reaction notes

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