Cyanoacetic acid → 6-Amino-1-cyclobutyl-2,4(1H,3H)-pyrimidinedione

HRID 236294Notes

Reaction equation

HRID 236294 reaction equation
[C:1]([CH2:3][C:4](O)=[O:5])#[N:2].[CH:7]1([NH:11][C:12]([NH2:14])=[O:13])[CH2:10][CH2:9][CH2:8]1>C(OC(=O)C)(=O)C>[NH2:2][C:1]1[N:11]([CH:7]2[CH2:10][CH2:9][CH2:8]2)[C:12](=[O:13])[NH:14][C:4](=[O:5])[CH:3]=1

Participants

4

Reactant 2

HCID 9740Cyanoacetic acidHCID 272625cyclobutylurea

Product 1

HCID 538833266-Amino-1-cyclobutyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 30 g (0.35 mol) cyanoacetic acid and 100 ml of acetic anhydride was added 36.1 g (0.32 mol) of cyclobutylurea. The solution was stirred at 60°-70° C. for 2 hours. After cooling, white crystals were filtered off and washed with ethanol. Yield 36.4 g (63%) (VII). This was suspended in 100 ml of hot water and 50 ml of 2N NaOH was added in portions so the solution the whole time was basic. The reaction mixture was refluxed for 20 minutes. After cooling, white crystals were filtered off. Yield 3.6 g (20%) (VIII) NMR.

Workup

  1. temperatureAfter cooling
  2. filtrationwhite crystals were filtered off
  3. washwashed with ethanol
  4. addition50 ml of 2N NaOH was added in portions so the solution the whole time
  5. temperatureThe reaction mixture was refluxed for 20 minutes
  6. temperatureAfter cooling
  7. filtrationwhite crystals were filtered off

Sources & evidence

ORD record
ord-0b19788f5bce4ed5b1862aee39896cd4
Source dataset
uspto-grants-1987_02
Patent number
US04644001

Reaction notes

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