Nitric Acid → 6-methyl-5-nitro-1,3-dipropyl-1H-pyrimidine-2,4-dione

HRID 269797Notes

Reaction equation

HRID 269797 reaction equation
[CH3:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH2:12][CH2:13][CH3:14])[C:4](=[O:15])[CH:3]=1.S(=O)(=O)(O)O.[N+:21]([O-])([OH:23])=[O:22]>>[CH3:1][C:2]1[N:7]([CH2:8][CH2:9][CH3:10])[C:6](=[O:11])[N:5]([CH2:12][CH2:13][CH3:14])[C:4](=[O:15])[C:3]=1[N+:21]([O-:23])=[O:22]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 11820436HCID 11820436, compound

Product 1

HCID 100379896-methyl-5-nitro-1,3-dipropyl-1H-pyrimidine-2,4-dione

Conditions

Temperature
0 °C

Procedure

1.2 g, 6 mmol, of 6-methyl-1,3-dipropyl-1,3-dihydropyrimidine-2,4-dione, as prepared in Example 1, was added in small portions to a cooled (0° C.) solution of concentrated sulfuric acid (3.0 ml) and nitric acid (2.0 ml). The reaction stirred at 0° C. for 2 hours. The reaction mixture was poured over ice and a green amorphous solid formed. The solid was removed by filtration and washed copiously with water. The solid was dissolved in dichloromethane and concentrated. The residue was purified using column chromatography (1:1.2 EtOAc:Hexanes) to yield 6-methyl-5-nitro-1,3-dipropyl-1,3-dihydropyrimidine-2,4-dione(0.430 g, HNMR)

Workup

  1. additionwas added in small portions to
  2. additionThe reaction mixture was poured over ice
  3. customa green amorphous solid formed
  4. customThe solid was removed by filtration
  5. washwashed copiously with water
  6. dissolutionThe solid was dissolved in dichloromethane
  7. concentrationconcentrated
  8. customThe residue was purified

Sources & evidence

ORD record
ord-d574cb588ec74ae5a30c2d0b271006e2
Source dataset
uspto-grants-2008_11
Patent number
US07449473B2

Reaction notes

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