Réaction #59343

Équation de réaction

sodium hydroxide

cyanoacetic acid

acetic anhydride

1-isobutyl-3-methylthiourea

→

6-amino-1-isobutyl-3-methyl-2-thioxo-1H-pyrimidin-4-one

Rendement 29.0%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   AutreThe solvent was evaporated
2. 2
   workup.DISSOLUTIONthe resulting red oil was redissolved in ethanol (5 mL)
3. 3
   TempératureThe reaction mixture was refluxed for 2 h
4. 4
   Autrethe resulting pale brown solid was purified by flash chromatography (ethyl acetate)

Mode opératoire

A solution of cyanoacetic acid (1.52 g, 17.8 mmol) in acetic anhydride (2.45 mL, 25.9 mmol) was added to 1-isobutyl-3-methylthiourea (2.37 g, 16.2 mmol). The reaction mixture was heated to 60° C. for 1.5 h. The solvent was evaporated and the resulting red oil was redissolved in ethanol (5 mL) and 5M sodium hydroxide (1.6 mL, 8.1 mmol) was added. The reaction mixture was refluxed for 2 h. The solvent was co-evaporated with ethanol and the resulting pale brown solid was purified by flash chromatography (ethyl acetate) to yield 6-amino-1-isobutyl-3-methyl-2-thioxo-1H-pyrimidin-4-one (1.0 g, 29%) as a yellow solid.

Source