Benzaldehyde → 1,3-Dimethyl-5-nitro-6-styryluracil

HRID 1784358Notes

Reaction equation

HRID 1784358 reaction equation
[CH3:1][N:2]1[C:7]([CH3:8])=[C:6]([N+:9]([O-:11])=[O:10])[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1CCCCC1>C(O)C>[CH3:1][N:2]1[C:7](/[CH:8]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:6]([N+:9]([O-:11])=[O:10])[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8082PiperidineHCID 7503695-Nitro-1,3,6-trimethyluracil

Product 1

HCID 53656311,3-Dimethyl-5-nitro-6-styryluracilYield 60.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,3,6-trimethyl-5-nitro-1H-pyrimidine-2,4dione (3.00 g, 15.06 mmol), benzaldehyde (1.58 ml, 15.56 mmol), piperidine (1.41 ml, 15.56 mmol) and a 3 Å molecular sieve (6.00 g) in ethanol (70 ml) was refluxed for 4 hours, filtered and the solid was treated with a mixture of chloroform and methanol. The resulting suspension was filtered again and the filtrates were evaporated. The residue was triturated with diethyl ether and the precipitate collected by filtration and dried under vacuum to yield 1,3-dimethyl-5-nitro-6-((E)styryl)-1H-pyrimidine-2,4-dione (2.61 g, 60%) as a yellow solid.

Workup

  1. filtrationfiltered
  2. additionthe solid was treated with a mixture of chloroform and methanol
  3. filtrationThe resulting suspension was filtered again
  4. customthe filtrates were evaporated
  5. customThe residue was triturated with diethyl ether
  6. filtrationthe precipitate collected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-8f03aa728ca143b69b12629aa0cc946b
Source dataset
uspto-grants-2009_03
Patent number
US07504398B2

Reaction notes

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