Ethyl cyanoacetate → 6-Amino-1-cyclopropylmethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one

HRID 31063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 31063
[CH:1]1([CH2:4][NH:5][C:6]([NH2:8])=[S:7])[CH2:3][CH2:2]1.C[O-].[Na+].[C:12]([CH2:14][C:15](OCC)=[O:16])#[N:13]>C(O)C>[NH2:13][C:12]1[N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[C:6](=[S:7])[NH:8][C:15](=[O:16])[CH:14]=1

Komponenten

5

Edukt 3

HCID 7764Ethyl cyanoacetateHCID 2795339N-CyclopropylmethylthioureaHCID 10942334Sodium Methoxide

Produkt 1

HCID 866010556-Amino-1-cyclopropylmethyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-oneAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 1-cyclopropylmethyl-2-thiourea (0.60 g, 4.6 mmol) in ethanol (10 mL) was added sodium methoxide (0.26 g, 4.8 mmol) and, after 5 minutes, ethyl cyanoacetate (0.50 mL, 4.6 mmol). The resulting mixture was heated to reflux for 2 h and 40 minutes followed by evaporation of the solvent under reduced pressure and treatment of the resulting yellow solid with 2M aqueous acetic acid (10 mL) giving a white solid. The solid was collected by filtration and washed with 2M aqueous acetic acid (10 mL), stirred with ethanol (10 mL) followed by evaporation and drying under reduced pressure, giving the title compound (0.51 g, 56%).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 h and 40 minutes
  3. customfollowed by evaporation of the solvent under reduced pressure and treatment of the resulting yellow solid with 2M aqueous acetic acid (10 mL)
  4. customgiving a white solid
  5. filtrationThe solid was collected by filtration
  6. washwashed with 2M aqueous acetic acid (10 mL)
  7. customfollowed by evaporation
  8. customdrying under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2e78d71160104c28a4a102b782dcc95d
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425560B2

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