Cyanoacetic acid → 6-Amino-1-butyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 1381853Notes

Reaction equation

HRID 1381853 reaction equation
[C:1]([CH2:3][C:4](O)=[O:5])#[N:2].[CH2:7]([NH:11][C:12]([NH2:14])=[O:13])[CH2:8][CH2:9][CH3:10]>C(OC(=O)C)(=O)C>[NH2:2][C:1]1[N:11]([CH2:7][CH2:8][CH2:9][CH3:10])[C:12](=[O:13])[NH:14][C:4](=[O:5])[CH:3]=1

Participants

4

Reactant 2

HCID 9740Cyanoacetic acidHCID 11595Butylurea

Product 1

HCID 24289966-Amino-1-butyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 46 g (0.55 mol) cyanoacetic acid and 100 ml of acetic anhydride was added 58 g (0.5 mol) of n-butylurea. The solution was stirred at 70° C. for 2 hours. After cooling white crystals were filtered off and washed with ethanol. Yield 68 g (74%) (VII). This was stirred in 500 ml of water and 20 ml of 5N NaOH was added in portions so the solution the whole time was basic. The reaction mixture was refluxed for 20 minutes and then neutralized with 5N HCl. After cooling, white crystals were filtered off. Yield 50.6 g (75%) (VIII), NMR.

Workup

  1. temperatureAfter cooling white crystals
  2. filtrationwere filtered off
  3. washwashed with ethanol
  4. stirringThis was stirred in 500 ml of water
  5. addition20 ml of 5N NaOH was added in portions so the solution the whole time
  6. temperatureThe reaction mixture was refluxed for 20 minutes
  7. temperatureAfter cooling
  8. filtrationwhite crystals were filtered off

Sources & evidence

ORD record
ord-d87e90a6f2664274a3c16f1ab5b6cdaf
Source dataset
uspto-grants-1989_02
Patent number
US04804664

Reaction notes

Loading…