Dimethylformamide dimethyl acetal → HCID 53948848, compound

HRID 476914Notes

Reaction equation

HRID 476914 reaction equation
[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH3:10])[C:4](=[O:11])[C:3]=1[C:12]#[N:13].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>CN(C)C=O>[C:12]([C:3]1[C:4](=[O:11])[N:5]([CH3:10])[C:6](=[O:9])[N:7]([CH3:8])[C:2]=1[N:1]=[CH:16][N:17]([CH3:19])[CH3:18])#[N:13]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 13296989HCID 13296989, compound

Product 1

HCID 53948848HCID 53948848, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.6 g (20 mmol) of 6-amino-5-cyano-1,3-dimethyluracil and 9.36 g (80 mmol) of dimethylformamide dimethyl acetal were added to 36 ml of dimethylformamide, and the reaction mixture was refluxed for 30 minutes. The solvent was removed by distillation under reduced pressure. The crude product was crystallized from ether, filtered off, and recrystallized from ethyl acetate to give 4.68 g of 5-cyano-6-dimethylaminomethyleneamino-1,3-dimethyluracil (compound 15) in a 99% yield.

Workup

  1. temperaturethe reaction mixture was refluxed for 30 minutes
  2. customThe solvent was removed by distillation under reduced pressure
  3. customThe crude product was crystallized from ether
  4. filtrationfiltered off
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-37c1a83c9479454b8ae0f8c0d0b09c13
Source dataset
uspto-grants-1989_12
Patent number
US04886807

Reaction notes

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