Réaction #40627

Équation de réaction

HCl

Sodium

4-[cyclohexyl-(2-ethoxycarbonyl-ethyl)-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester

sodium t-butoxide

→

title compound

Rendement 63.0%

8-Cyclohexyl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Rendement 63.0%

Solvants

t-butanol

toluene

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was then cooled
2. 2
   ExtractionThe solution was then extracted with EtOAc (2×20 mL)
3. 3
   Séchagethe organic layer was dried (MgSO4)
4. 4
   Concentrationconcentrated

Mode opératoire

Sodium (25 wt % dispersion in paraffin wax, 0.10 g, 3.8 mmol) was added to t-butanol (1.8 mL) at rt. After 10 minutes, a solution of 4-[cyclohexyl-(2-ethoxycarbonyl-ethyl)-amino]-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (1.0 g, 2.5 mmol) in 10 mL of toluene was added to the sodium t-butoxide solution and the resulting mixture was heated at 90° C. for 30 minutes. The reaction mixture was then cooled and the solution was adjusted to pH 7 using a 1N HCl solution. The solution was then extracted with EtOAc (2×20 mL) and the organic layer was dried (MgSO4) and concentrated to provide 0.55 g (42%) of the title compound.

Source