Nitric Acid → 6-methyl-5-nitro-3-propyl-1,3-dihydropyrimidine-2,4-dione

HRID 269795Notes

Reaction equation

HRID 269795 reaction equation
[CH2:1]([N:4]1[C:9](=[O:10])[CH:8]=[C:7]([CH3:11])[NH:6][C:5]1=[O:12])[CH2:2][CH3:3].OS(O)(=O)=O.[N+:18]([O-])([OH:20])=[O:19]>O>[CH3:11][C:7]1[NH:6][C:5](=[O:12])[N:4]([CH2:1][CH2:2][CH3:3])[C:9](=[O:10])[C:8]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 165610Uracil, 6-methyl-4-propyl-

Product 1

HCID 102626226-methyl-5-nitro-3-propyl-1,3-dihydropyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-propyl-6-methyl-1,3-dihydropyrimidine-2,4-dione (3 g), as prepared in Example 3, was added to a solution of concentrated H2SO4 (12 ml) and HNO3 (9.6 ml) at 0° C. The reaction mixture was allowed to come to room temperature and continued stirring for another 2 h. The reaction mixture was then poured into water and extracted with ethyl acetate (3×50 mL). The organic layer was washed with water, brine and dried over Na2SO4. Removal of the solvent and recrystallization of the residue with ethylacetate/hexane mixture furnished the 6-methyl-5-nitro-3-propyl-1,3-dihydropyrimidine-2,4-dione(1.56 g).

Workup

  1. customto come to room temperature
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent and recrystallization of the residue with ethylacetate/hexane mixture

Sources & evidence

ORD record
ord-36a7fa056d7a45c28b40a06e951abd6c
Source dataset
uspto-grants-2008_11
Patent number
US07449473B2

Reaction notes

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