Nitric Acid → HCID 15485643, compound

HRID 367265Notes

Reaction equation

HRID 367265 reaction equation
[CH2:1]([N:5]1[C:10]([CH3:11])=[CH:9][C:8](=[O:12])[N:7]([CH3:13])[C:6]1=[O:14])[CH2:2][CH2:3][CH3:4].[N+:15]([O-])([OH:17])=[O:16]>OS(O)(=O)=O>[CH2:1]([N:5]1[C:10]([CH3:11])=[C:9]([N+:15]([O-:17])=[O:16])[C:8](=[O:12])[N:7]([CH3:13])[C:6]1=[O:14])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 15485642HCID 15485642, compound

Product 1

HCID 15485643HCID 15485643, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To 1.69 g (8.61 mmol) of 1-butyl-3,6-dimethyl-1H-pyrimidine-2,4-dione in 30 mL concentrated H2SO4 at 0° C. was added 1.7 mL fuming HNO3 in drops over 10 min. After stirring at 0° C. for an additional 30 min, the reaction mixture was poured into 300 mL of ice, extracted with 2×150 mL CH2Cl2, and the combined organics were dried over MgSO4, filtered and evaporated to a yellow oil. Flash chromatography on silica gel, eluting with CH2Cl2 /EtOAc (40/1), gave 1.72 g (7.13 mmol, an 83% yield) of the title compound as a light yellow oil. 1H NMR (300 MHz, CDCl3): δ 0.99 (t, J=7.3 Hz, 3H), 1.46 (hex, J=7.3 Hz, 2H), 1.62-1.73 (m, 2H), 2.42 (s, 3H), 3.39 (s, 3H), 3.92 (t, J=7.4 Hz, 2H); IR (KBr, cm-1): 2961s, 2874s, 1722s, 1670s, 1620s, 1363s, 1224m; MS (ES) m/z (relative intensity): 242 (M+ +H, 100). Anal. Calcd for C10H15N3O4 : C, 49.79; H, 6.27, N, 17.42. Found: C, 49.47; H, 6.03; N, 17.37.

Workup

  1. customover 10 min
  2. extractionextracted with 2×150 mL CH2Cl2
  3. dry with materialthe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to a yellow oil
  6. washFlash chromatography on silica gel, eluting with CH2Cl2 /EtOAc (40/1)
  7. customgave 1.72 g (7.13 mmol

Sources & evidence

ORD record
ord-cc4872f667d84ae7bd960cca473c8551
Source dataset
uspto-grants-2000_10
Patent number
US06133273

Reaction notes

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