反应详情

A mixture of 0.8 g of 4-chloro-5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneamino-pyrimidine, 35 mL acetonitrile and 0.71 g 1-acetyl piperazine was refluxed for one and one half hours. A green solution initially forms and the color changes to amber on continued heating. The solution was evaporated in vacuo and partitioned between dichloromethane and water. The organic phase was washed twice with water, dried over sodium sulfate, filtered and evaporated. The orange-brown brittle foam obtained was purified by column chromatography on silica gel, eluting initially with dichloromethane and then with 15% methanol/dichloromethane to give the intermediate derivative, 4-(-4-acetyl piperazino)-5-(4-chlorophenylethynyl)-2-diisopropylaminomethyleneaminopyrimidine. Heating 0.6 g of the intermediate with 40 mL methanolic ammonia in a bomb at 120° C. for 18 hours gave on evaporation in vacuo, a cocoa-colored residue which was purified by column chromatography on silica gel. The desired product 4-(4-acetylpiperazino)-2-amino-5-(4-chlorophenylethynyl)pyrimidine was obtained by elution with 5% methanol/dichloromethane, evaporation and trituration with methanol yielding 0.27 g, m.p. 165° C.

1. temperaturewas refluxed for one and one half hours
2. customThe solution was evaporated in vacuo
3. custompartitioned between dichloromethane and water
4. washThe organic phase was washed twice with water
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated
8. customThe orange-brown brittle foam obtained
9. customwas purified by column chromatography on silica gel
10. washeluting initially with dichloromethane