Acetic Anhydride → 6-Amino-1,3-diethyl-2,4(1H,3H)-pyrimidinedione

HRID 574125Notes

Reaction equation

HRID 574125 reaction equation
[CH2:1]([NH:3][C:4](=[O:8])[NH:5][CH2:6][CH3:7])[CH3:2].[C:9](CC(O)=O)#[N:10].C(O[C:19](=[O:21])[CH3:20])(=O)C>>[NH2:10][C:9]1[N:5]([CH2:6][CH3:7])[C:4](=[O:8])[N:3]([CH2:1][CH3:2])[C:19](=[O:21])[CH:20]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 9740Cyanoacetic acidHCID 12194sym-Diethylurea

Product 1

HCID 6030266-Amino-1,3-diethyl-2,4(1H,3H)-pyrimidinedione

Procedure

12.69 grams (0.14 mol) of diethylurea and 11.90 grams (0.14 mol) of cyanoacetic acid were heated in acetic anhydride at 60° C. for 3 hours, under dry atmosphere. Thereafter, the acetic anhydride and remaining cyanoacetic acid were evaporated, 5% sodium hydroxide was added and the mixture was stirred and cooled. 20 grams of 6-amino-1,3-diethyluracil were obtained as a precipitate. 11.8 grams of sodium nitrite in 70 ml water were then added while cooling and stirring and the solution was then acidified by adding 70 ml acetic acid. The mixture was stirred at room temperature for additional 2.5 hours. The resulting precipitate was filtered, washed with water, ethanol and finally ether so afford 10.1 grams of 6-amino-1,3-diethyl-5-nitrosouracil, as a violet product.

Workup

  1. customunder dry atmosphere
  2. customwere evaporated
  3. addition5% sodium hydroxide was added
  4. temperaturecooled

Sources & evidence

ORD record
ord-2c8a55c244184394a7894919c1f4cab0
Source dataset
uspto-grants-2015_05
Patent number
US09034872B2

Reaction notes

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