تفاعل #74160

معادلة التفاعل

1-(4-methoxybenzyl)-3-(3-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

2-methylthio-4-chloro-pyrimidine

cesium carbonate

→

title compound

المردود 88.4%

4-[1-(4-methoxybenzyl)-3-(3-nitrophenyl)-1H-pyrazol-4-yl]-2-(methylsulfanyl)-pyrimidine

المردود 88.4%

المذيبات

dioxane

water

ظروف التفاعل

المعالجة

1. 1
   ترشيحfiltered through a celite pad
2. 2
   تركيزconcentrated under reduced pressure
3. 3
   أخرىThe residue was partitioned between dichloromethane and water
4. 4
   تجفيفthe organic layer dried over sodium sulphate
5. 5
   أخرىevaporated to dryness
6. 6
   أخرىThe crude was finally purified by flash-chromatography on a silica gel column (cyclohexane-ethylacetate; from 9/1 to 4/1)

الإجراء التجريبي

2.6 g (6 mmol) of 1-(4-methoxybenzyl)-3-(3-nitrophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole were dissolved in a mixture of 520 ml of dioxane and 130 ml of water under a nitrogen atmosphere. 709 μl (6 mmol) of 2-methylthio-4-chloro-pyrimidine, 3.9 g (12 mmol) of cesium carbonate and 650 mg (0.6 mmol) of palladium tetrakis were added consecutively to the resulting solution under stirring. The reaction mixture was heated at 100° C. for 6 hours, then filtered through a celite pad and concentrated under reduced pressure. The residue was partitioned between dichloromethane and water, the organic layer dried over sodium sulphate and evaporated to dryness. The crude was finally purified by flash-chromatography on a silica gel column (cyclohexane-ethylacetate; from 9/1 to 4/1), giving 2.3 g (88%) of the title compound.

المصدر