Reacción #214567

Ecuación de reacción

4-allylamino-2-methylthio-5-pyrimidine carboxylic acid ethyl ester

ethyl malonyl chloride

diethyl ether

→

7,8-dihydro-5-hydroxy-2-(methylthio)-7-oxo-8-(2-propenyl)pyrido-[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe mixture was filtered
2. 2
   Otrothe filtrate was evaporated in a rotary evaporator
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 15 ml
4. 4
   workup.ADDITIONof ethanol and this solution was added to a solution of 2.3 g
5. 5
   workup.STIRRINGThe mixture was stirred at room temperature for 5 minutes
6. 6
   workup.ADDITIONwas diluted with water
7. 7
   Extracciónwas extracted with 150 ml
8. 8
   SecadoThe ether layer was dried over magnesium sulfate
9. 9
   Filtraciónfiltered
10. 10
    FiltraciónThe mixture was filtered
11. 11
    Temperaturathe filtrate was cooled in ice
12. 12
    OtroThe precipitate which formed
13. 13
    Otrowas collected
14. 14
    Otrowas recrystallized from ethyl acetate
15. 15
    Otroto give 0.2 g

Procedimiento

To a solution of 25.3 g. (0.1 mole) of 4-allylamino-2-methylthio-5-pyrimidine carboxylic acid ethyl ester in 400 ml. of anhydrous diethyl ether was added 7.5 g. (0.005 mole) of ethyl malonyl chloride. The mixture was stirred at room temperature for 3 hours. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was dissolved in 15 ml. of ethanol and this solution was added to a solution of 2.3 g. (0.1 g. atom) of sodium in 200 ml. of ethanol. The mixture was stirred at room temperature for 5 minutes and was diluted with water, acidified with glacial acetic acid and was extracted with 150 ml. of diethyl ether. The ether layer was dried over magnesium sulfate, filtered and was acidified with gaseous hydrogen chloride. The mixture was filtered and the filtrate was cooled in ice. The precipitate which formed was collected and was recrystallized from ethyl acetate to give 0.2 g. of product--m.p. 134°-136° C.

Fuente