Nitric Acid → 2-Amino-5-nitropyrimidin-4(1H)-one

HRID 1398488Notes

Reaction equation

HRID 1398488 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[NH:12][C:11](=[O:13])[CH:10]=[CH:9][N:8]=1.[N+:14]([O-])([OH:16])=[O:15]>O>[NH2:6][C:7]1[NH:12][C:11](=[O:13])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 66950Isocytosine

Product 1

HCID 2520912-Amino-5-nitropyrimidin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Concentrated sulfuric acid (2.4 mL) was added to 2-amino-3,4-dihydropyrimidin-4-one (1 g, 9.0 mmol). The mixture was stirred and cooled in ice bath before dropwise addition of concentrated nitric acid (0.56 mL). The mixture was stirred at RT for 30 min before being heated at 70° C. for 2 hr. The mixture was allowed to cool to RT and was slowly added to water (10 mL), cooled in an ice bath. The resultant precipitate was collected by suction filtration, washed with diethyl ether (5 mL) and then thoroughly dried under high vacuum to give the title compound: 1H NMR (250 MHz, DMSO) δ 7.18 (1H, br. s.), 8.61 (1H, br. s.), 8.81 (1H, s); LC-MS: m/z=+156.9 (M+H)+.

Workup

  1. temperaturecooled in ice bath
  2. stirringThe mixture was stirred at RT for 30 min
  3. temperatureto cool to RT
  4. temperaturecooled in an ice bath
  5. filtrationThe resultant precipitate was collected by suction filtration
  6. washwashed with diethyl ether (5 mL)
  7. customthoroughly dried under high vacuum

Sources & evidence

ORD record
ord-fc55557d0e514d18a5d79413104758a0
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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