Reacción #1146817

Ecuación de reacción

S-ethylisothiourea hydroiodide

ethoxymethylidenemalo-nonitrile

NaOMe

→

4-amino-5-cyano-2-ethylthiopyrimidine

Rendimiento 45.0%

Disolventes

ethanol

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture is refluxed under N2 for 2 h
2. 2
   Concentraciónthe solution is concentrated on a hot plate until precipitation
3. 3
   TemperaturaAfter cooling
4. 4
   Filtraciónthe solid is collected by suction filtration
5. 5
   FiltraciónFiltration and vacuum oven
6. 6
   Otrodrying

Procedimiento

A suspension of NaOMe (2.7 g, 50 mmol) in EtOH (200 mL) is added to a mixture of S-ethylisothiourea hydroiodide (11.58 g, 50 mmol), ethoxymethylidenemalo-nonitrile (6.1 g, 50 mmol) and ethanol (250 mL) at 25° C. The reaction mixture is refluxed under N2 for 2 h, and then the solution is concentrated on a hot plate until precipitation is observed. After cooling, the solid is collected by suction filtration and is stirred in water at 25° C. Filtration and vacuum oven drying affords 4-amino-5-cyano-2-ethylthiopyrimidine (4.02 g, 45%) as a brown solid. 1H NMR δ (DMSO) 8.45 (1H, s), 7.90 (2H, brs), 3.00 (2H, q, J=7.3 Hz), 1.27 (3H, t, J=7.3 Hz).

Fuente