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

HRID 1801700Notes

Reaction equation

HRID 1801700 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-d55a39443cf44571ac47234f37a97010
Source dataset
uspto-grants-2013_01
Patent number
US08349850B2

Reaction notes

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