反応 #56815

反応方程式

ethyl acetate

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

4-bromoaniline

→

title compound

収率 59.0%

N*4*-(4-Bromo-phenyl)-6-(2,5-dichloro-phenyl)-pyrimidine-2,4-diamine

収率 59.0%

溶媒

ethanol

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度under reflux for 1 hour
3. 3
   その他After evaporation of the solvent under reduced pressure
4. 4
   workup.ADDITIONthe residue was treated with 1.0 N hydrochloric acid (10 ml)
5. 5
   ろ過Filtration
6. 6
   その他provided the crude product, which
7. 7
   workup.STIRRINGstirred for 1 hour
8. 8
   ろ過After filtration the solid
9. 9
   workup.DISSOLUTIONwas dissolved in methanol (10 ml)
10. 10
    workup.ADDITIONtreated with aqueous sodium carbonate solution (1.0 M, 1 ml)
11. 11
    workup.STIRRINGAfter stirring for 1 hour
12. 12
    その他the solvent was evaporated under reduced pressure
13. 13
    workup.ADDITIONthe solid was treated with water (10 ml)
14. 14
    workup.STIRRINGAfter stirring for 15 minutes
15. 15
    ろ過filtration

実験手順

A mixture of the hydrochloride salt of 4-chloro-6-(2,5-dichloro-phenyl)-pyrimidin-2-yl-amine (0.03 g, 0.096 mmol) and 4-bromoaniline (0.034 g, 0.020 mmol) in ethanol (7.5 ml) was heated under reflux for 1 hour. After evaporation of the solvent under reduced pressure, the residue was treated with 1.0 N hydrochloric acid (10 ml) and stirred for 30 minutes. Filtration provided the crude product, which was treated with ethyl acetate (10 ml) and stirred for 1 hour. After filtration the solid was dissolved in methanol (10 ml) and treated with aqueous sodium carbonate solution (1.0 M, 1 ml). After stirring for 1 hour, the solvent was evaporated under reduced pressure and the solid was treated with water (10 ml). After stirring for 15 minutes, filtration provided the title compound (59% yield) as a white powder. 1H NMR (DMSO-d6) δ 6.31 (s, 1H, Ar), 6.54 (s, 2H, NH2), 7.45 (d, 2H, J=8.9 Hz, Ar), 7.52 (dd, 1H, J=8.6 Hz, J-2.6 Hz, Ar), 7.60 (d, 1H, J=8.6 Hz, Ar), 7.64 (d, 1H, J=2.6 Hz, Ar), 7.77 (d, 2H, J=8.9 Hz, Ar), 9.46 (s, 1H, NH).

出典