Nitric Acid → 5-Nitro-1,3,6-trimethyluracil

HRID 467845Notes

Reaction equation

HRID 467845 reaction equation
OS(O)(=O)=O.[N+:6]([O-:9])(O)=[O:7].[CH3:10][N:11]1[C:16]([CH3:17])=[CH:15][C:14](=[O:18])[N:13]([CH3:19])[C:12]1=[O:20]>>[CH3:10][N:11]1[C:16]([CH3:17])=[C:15]([N+:6]([O-:9])=[O:7])[C:14](=[O:18])[N:13]([CH3:19])[C:12]1=[O:20]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 260751,3,6-Trimethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 7503695-Nitro-1,3,6-trimethyluracil

Conditions

Temperature
2.5 °C

Procedure

A mixture of concentrated H2SO4 (7.0 mL) and fuming HNO3 (7.0 mL) was cooled to 0-5° C. and 1,3,6-trimethylpyrimidine-2,4(1H,3H)-dione (3.5 g, 22.702 mmol) was gradually added to the reaction mixture. After stirring for 2 h. at the same temperature the reaction mixture was partitioned between ethyl acetate (200 mL) and water (100 mL). The organic layer was washed with brine (2×50 mL), dried (Na2SO4) and evaporated under reduced pressure. Crude product obtained was purified by column chromatography to give 1.30 g of the product as yellow solid; 1H NMR (δ ppm, 300 MHz, DMSO-d6) 2.38 (s, 3H), 3.20 (s, 3H), 3.40 (s, 3H); APCI-MS (m/z) 198.30 (M−H).

Workup

  1. customwas partitioned between ethyl acetate (200 mL) and water (100 mL)
  2. washThe organic layer was washed with brine (2×50 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customCrude product obtained
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-23d50f8340db4d71b8a4f1b72e293ce8
Source dataset
uspto-grants-2014_01
Patent number
US08623880B2

Reaction notes

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