Potassium Nitrate → 1,6-Dimethyl-5-nitrouracil

HRID 60340Notes

Reaction equation

HRID 60340 reaction equation
[CH3:1][N:2]1[C:7]([CH3:8])=[CH:6][C:5](=[O:9])[NH:4][C:3]1=[O:10].[N+:11]([O-])([O-:13])=[O:12].[K+]>OS(O)(=O)=O>[CH3:1][N:2]1[C:7]([CH3:8])=[C:6]([N+:11]([O-:13])=[O:12])[C:5](=[O:9])[NH:4][C:3]1=[O:10]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 106068181,6-Dimethyluracil

Product 1

HCID 136130661,6-Dimethyl-5-nitrouracilYield 68.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1,6-dimethylpyrimidine-2,4(1H,3H)-dione (5 g, 0.035 mol) in H2SO4 (20 mL) at 0° C. was added dropwise a solution of KNO3 (4.69 g, 0.046 mol) in H2SO4 (10 mL). The reaction was stirred 0° C. for 2 h, warmed to RT, stirred for 18 h, poured into ice then extracted with EA (5×50 mL). The combined organic layers were dried over Na2SO4, and concentrated to give 1,6-dimethyl-5-nitropyrimidine-2,4(1H,3H)-dione (4.3 g, 68.1% yield) as a yellow solid. 1H NMR (DMSO-d6) δ: 12.09 (s, 1H), 3.32 (s, 3H), 2.36 (s, 3H) LCMS: MH+ 186 and TR=0.610 min. Used without further purification.

Workup

  1. temperaturewarmed to RT
  2. stirringstirred for 18 h
  3. additionpoured into ice
  4. extractionthen extracted with EA (5×50 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5399fda61c6b40a8a55dfa61148b7666
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

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