반응 #3325

반응 방정식

NaH

ethyl acetate

2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one

Methyl 4-(bromomethyl) benzoate

→

4-[2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-ylmethyl]-benzoic acid methyl ester

수율 70.0%

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도The mixture was heated at 40° C. to 50° C. for 20 minutes
2. 2
   기타resulting in a clear solution
3. 3
   온도the reaction mixture was heated at 40° C. to 50° C. for 15 minutes
4. 4
   기타The resulting precipitate was removed by filtration
5. 5
   세척washed with water
6. 6
   기타The solid was purified by flash chromatography
7. 7
   세척eluting with a gradient of 1:1 hexane
8. 8
   건조ethyl acetate to 1:2 hexane: ethyl acetate, then dried in vacuo

실험 절차

To a suspension of NaH (60% in mineral oil, 36 mg) in 7 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (195 mg, 0.64 mmol). The mixture was heated at 40° C. to 50° C. for 20 minutes, resulting in a clear solution. Methyl 4-(bromomethyl) benzoate (206 mg, 0.90 mmol) was added, and the reaction mixture was heated at 40° C. to 50° C. for 15 minutes, then poured onto 30 mL of ice water. The resulting precipitate was removed by filtration and washed with water. The solid was purified by flash chromatography, eluting with a gradient of 1:1 hexane:ethyl acetate to 1:2 hexane: ethyl acetate, then dried in vacuo to provide 204 mg of 4-[2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-ylmethyl]-benzoic acid methyl ester containing 0.16 equivalents of ethyl acetate; mp 235°-237° C.

출처