تفاعل #56917

معادلة التفاعل

2,3,5-trichloro-phenyl boronic acid

4,6-dichloro-pyrimidin-2-yl-amine

sodium carbonate

triphenylphosphine

→

4-chloro-6-(2,3,5-trichloro-phenyl)-pyrimidin-2-yl-amine-hydrochloride salt

المردود 40.4%

المذيبات

ethylene glycol dimethyl ether

water

acetone

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was stirred for 18 hours
2. 2
   ترشيحfiltered through a pad of celite under suction
3. 3
   تركيزconcentrated under reduced pressure
4. 4
   workup.ADDITIONThe residue was treated with water (100 ml)
5. 5
   workup.STIRRINGthe mixture was stirred vigorously
6. 6
   ترشيحThe solid was filtered
7. 7
   workup.DISSOLUTIONdissolved in tetrahydrofuran (100 ml)
8. 8
   workup.ADDITIONHydrogen chloride (4 M in dioxane, 20 ml) was added
9. 9
   workup.STIRRINGAfter stirring for 1 hour
10. 10
    ترشيحthe solid was filtered
11. 11
    أخرىdried under reduced pressure
12. 12
    workup.ADDITIONThe solid was treated with ethyl acetate (50 ml)
13. 13
    workup.STIRRINGstirred for 30 minutes
14. 14
    ترشيحThe solid was filtered
15. 15
    أخرىdried under reduced pressure

الإجراء التجريبي

A mixture of 2,3,5-trichloro-phenyl boronic acid (12 g, 53 mmol) and 4,6-dichloro-pyrimidin-2-yl-amine (10.5 g, 64 mmol) in ethylene glycol dimethyl ether (300 ml) under Argon atmosphere was stirred for 30 minutes. A mixture of palladium (II) acetate (1.8 g, 8 mmol), a solution of sodium carbonate (28.2 g, 270 mmol) in water (100 ml), and triphenylphosphine (4.2 g, 16 mmol) were added and the mixture was stirred for 18 hours. The mixture was treated with acetone (500 ml), filtered through a pad of celite under suction and concentrated under reduced pressure. The residue was treated with water (100 ml) and the mixture was stirred vigorously. The solid was filtered and dissolved in tetrahydrofuran (100 ml). Hydrogen chloride (4 M in dioxane, 20 ml) was added. After stirring for 1 hour, the solid was filtered and dried under reduced pressure. The solid was treated with ethyl acetate (50 ml) and stirred for 30 minutes. The solid was filtered and dried under reduced pressure to afford 4-chloro-6-(2,3,5-trichloro-phenyl)-pyrimidin-2-yl-amine-hydrochloride salt (3.7 g, 20% yield) as a white powder.

المصدر