Reacción #340227

Ecuación de reacción

compound ( 10 )

methyl 4-(4′-fluorophenyl)-6-isopropyl-2-methylthio-pyrimidin-5-yl-carboxylate

methyl 4-(4′-fluorophenyl)-6-isopropyl-2-methylthio-pyrimidin-5-yl-carboxylate

toluene

diisobutyl aluminum hydride

→

white crystal

Rendimiento 88.0%

4-(4′-fluorophenyl)-6-isopropyl-2-methylthio-5-hydroxymethyl-pyrimidine

Rendimiento 88.0%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroequipped with a mechanical stirrer
2. 2
   Temperaturawhile cooling in an ice-salt bath
3. 3
   Otrofurther reacted for 2-3 hours
4. 4
   Otrothe organic layer was collected
5. 5
   Lavadowashed with water (200 mL×2)
6. 6
   Secadoa saturated solution of sodium chloride (200 mL×1), and then dried overnight over anhydrous magnesium sulfate
7. 7
   FiltraciónThe mixture was then filtered
8. 8
   Otroevaporated under reduced pressure
9. 9
   Otroto remove the solvent
10. 10
    Otrorecrystallized in ethyl acetate

Procedimiento

20 g (62.5 mmol) of methyl 4-(4′-fluorophenyl)-6-isopropyl-2-methylthio-pyrimidin-5-yl-carboxylate (10) and 300 mL of dry anhydrous toluene were loaded in a IL three-neck round bottomed flask, equipped with a mechanical stirrer and an air duct, and stirred under a nitrogen atmosphere. 100 mmol of diisobutyl aluminum hydride (DIBAI-H) was then added in batches into the mixture while cooling in an ice-salt bath. After TLC assay showed that the starting compound (10) was depleted, the reaction mixture was warmed up to room temperature and further reacted for 2-3 hours. 500 mL of water was then added, and the organic layer was collected, washed with water (200 mL×2) and a saturated solution of sodium chloride (200 mL×1), and then dried overnight over anhydrous magnesium sulfate. The mixture was then filtered, evaporated under reduced pressure to remove the solvent, and recrystallized in ethyl acetate, obtaining 16 g of a white crystal, yield 88%.

Fuente