Réaction #162813

Équation de réaction

3-cyclopropyl-5-hydroxy-8-methyl-1-(3-nitrophenyl)-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione

acetonitrile

tosyl chloride

→

toluene-4-sulfonic acid 3-cyclopropyl-8-methyl-1-(3-nitrophenyl)-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester

Rendement 82.4%

Solvants

triethylamine

Conditions de réaction

Traitement

1. 1
   Températurewith heating
2. 2
   ConcentrationThe reaction mixture was concentrated under reduced pressure
3. 3
   workup.ADDITIONWater (100 ml) was added to the residue
4. 4
   Extractionthe mixture was extracted with chloroform (800 ml)
5. 5
   LavageThe organic layer was washed with brine (50 ml)
6. 6
   Séchagedried over anhydrous magnesium sulfate
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   AutreThe residue was recrystallized from chloroform

Mode opératoire

To 3-cyclopropyl-5-hydroxy-8-methyl-1-(3-nitrophenyl)-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione 10 (18 g) obtained in Step 5 were added acetonitrile (180 ml), tosyl chloride 11 (11 g) and triethylamine (8 ml), and the mixture was stirred with heating under reflux at 110° C. for 1 hr. The reaction mixture was concentrated under reduced pressure. Water (100 ml) was added to the residue and the mixture was extracted with chloroform (800 ml). The organic layer was washed with brine (50 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from chloroform:diethyl ether=1:5 to give toluene-4-sulfonic acid 3-cyclopropyl-8-methyl-1-(3-nitrophenyl)-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester 12 (21 g, 82%) as a white solid.

Source