تفاعل #56816

معادلة التفاعل

4,6-dichloro-2-amino-pyrimidine

5-chloro-2-methyl-phenyl boronic acid

triphenylphosphine

sodium carbonate

→

4-chloro-6-(5-chloro-2-methyl-phenyl) pyrimidin-2-yl-amine

المردود 40.3%

المذيبات

acetone

water

glyme

ظروف التفاعل

المعالجة

1. 1
   ترشيحthe mixture was filtered through a pad of celite under suction
2. 2
   تركيزthe filtrate was concentrated under vacuum
3. 3
   أخرىThe residual solid was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:9)
4. 4
   تركيزAfter concentration under reduced pressure
5. 5
   workup.DISSOLUTIONthe solid was dissolved in methanol
6. 6
   workup.ADDITIONa solution of hydrogen chloride in dioxane (4.0 M, 5 ml) was added
7. 7
   تركيزAfter concentration under vacuum
8. 8
   workup.ADDITIONthe solid was treated with ethyl acetate (5 ml)
9. 9
   workup.STIRRINGstirred for one hour
10. 10
    ترشيحFiltration

الإجراء التجريبي

To a mixture of 4,6-dichloro-2-amino-pyrimidine (0.481 g, 2.93 mmol), 5-chloro-2-methyl-phenyl boronic acid (0.5 g, 2.93 mmol), palladium (II) acetate (0.1 g, 0.44 mmol), and triphenylphosphine (0.23 g, 0.88 mmol) was added a solution of sodium carbonate (1.5 g, 14.6 mmol) in water (5.0 ml) followed by glyme (20 ml). The mixture was stirred under an argon atmosphere for 16 hours. After addition of acetone (15 ml), the mixture was filtered through a pad of celite under suction and the filtrate was concentrated under vacuum. The residual solid was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:9). After concentration under reduced pressure, the solid was dissolved in methanol and a solution of hydrogen chloride in dioxane (4.0 M, 5 ml) was added. After concentration under vacuum, the solid was treated with ethyl acetate (5 ml) and stirred for one hour. Filtration provided the hydrochloride salt of 4-chloro-6-(5-chloro-2-methyl-phenyl) pyrimidin-2-yl-amine (0.30 g, 35% yield) as a white powder.

المصدر