Reaction #40628

Reaction equation

Bromine

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

diisopropylethylamine

→

title compound

Yield 102.0%

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

Yield 102.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Concentrationthe solution was concentrated
2. 2
   workup.DISSOLUTIONthe crude residue was redissolved in dichloromethane (10 mL)
3. 3
   workup.WAITAfter 15 h
4. 4
   Otherthe reaction mixture was partitioned between water and dichloromethane
5. 5
   Otherthe organic layer was separated
6. 6
   Dryingdried (MgSO4)
7. 7
   Concentrationconcentrated

Procedure

Bromine (0.15 g, 0.94 mmol) was added to a solution of 8-cyclohexyl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.28 g, 0.79 mmol) in dichloromethane (10 mL). After 5 min, the solution was concentrated and the crude residue was redissolved in dichloromethane (10 mL) and diisopropylethylamine (0.42 mL, 2.4 mmol) was added. After 15 h, the reaction mixture was partitioned between water and dichloromethane, the organic layer was separated, dried (MgSO4) and concentrated to provide 0.28 g (87%) of the title compound. Mass Spectrum (LCMS, ESI pos.) Calcd. For C17H21N3O3S: 347.13. found: (M+H) 348.3.

Source