反応 #3323

反応方程式

Diethyl ether

[2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-yl]-acetic acid tert-butyl ester

trifluoroacetic acid

→

[2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-yl]-acetic acid

収率 52.5%

溶媒

methylene chloride

反応条件

後処理

1. 1
   濃縮concentrated in vacuo
2. 2
   その他The resultant oil was partitioned between methylene chloride and brine
3. 3
   洗浄The aqueous layer was washed with ethyl acetate
4. 4
   乾燥dried over magnesium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated in vacuo
7. 7
   その他to give a gummy solid
8. 8
   その他the resultant precipitate was collected
9. 9
   workup.ADDITIONHexane was added to the filtrate
10. 10
    その他once again the resultant precipitate was collected
11. 11
    その他dried in vacuo at 80° C.

実験手順

To a solution of [2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-yl]-acetic acid tert-butyl ester (157 mg, 0.37 mmol) from Example 36 in 4 mL of methylene chloride was added 2 mL of trifluoroacetic acid. The solution was stirred at room temperature for 5 hours, then concentrated in vacuo. The resultant oil was partitioned between methylene chloride and brine. The aqueous layer was washed with ethyl acetate, and the organic layers were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo to give a gummy solid. Diethyl ether was added, and the resultant precipitate was collected. Hexane was added to the filtrate, and once again the resultant precipitate was collected. The solids were combined and dried in vacuo at 80° C. to give 71 mg (52%) of [2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-yl]-acetic acid that was >97% pure by HPLC; mp 297°-300° C. dec.

出典