Nitric Acid → HCID 66955389, compound

HRID 1399724Notes

Reaction equation

HRID 1399724 reaction equation
[N+]([O-])(O)=O.[CH3:5][C:6]1[NH:11][C:10](=[O:12])[NH:9][CH:8]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:7]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:5][C:6]1[NH:11][C:10](=[O:12])[N:9]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:7]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 11430Potassium CarbonateHCID 296187Ethyl 6-methyl-4-(4-methylphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Product 1

HCID 66955389HCID 66955389, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cold (0° C.) mixture of nitric acid (70%) (34 ml) and water (6 mL) was added ethyl 6-methyl-2-oxo-4-p-tolyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate (6 g; 21,87 mmol) in small portions (within 3 min). The mixture was stirred for 30 min while gradually allowed to reach room temperature. The reaction was poured onto crushed ice and neutralized by adding potassium carbonate until pH 8. The aqueous layer was extracted with chloroform (3 times) and the combined organics were dried over sodium sulphate, filtered and concentrated under reduced pressure. The obtained green oil was dissolved in dichloromethane and concentrated under reduced pressure to afford a green solid, which was crystallized from ethanol and the obtained greenish crystals were triturated with heptane to furnish 3.7 g (60%) of the title compound as a white-to-green solid.

Workup

  1. customto reach room temperature
  2. additionThe reaction was poured
  3. customonto crushed ice
  4. extractionThe aqueous layer was extracted with chloroform (3 times)
  5. dry with materialthe combined organics were dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe obtained green oil was dissolved in dichloromethane
  9. concentrationconcentrated under reduced pressure
  10. customto afford a green solid, which
  11. customwas crystallized from ethanol
  12. customthe obtained greenish crystals were triturated with heptane

Sources & evidence

ORD record
ord-bf8f13adba48455a80539acf3f166015
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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