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

HRID 236294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236294
[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

Komponenten

4

Edukt 2

HCID 9740Cyanoacetic acidHCID 272625cyclobutylurea

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0b19788f5bce4ed5b1862aee39896cd4
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04644001

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