반응 #3323

반응 방정식

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

수율 52.5%

용매

methylene chloride

반응 조건

후처리

1. 1
   농축concentrated in vacuo
2. 2
   기타The resultant oil was partitioned between methylene chloride and brine
3. 3
   세척The aqueous layer was washed with ethyl acetate
4. 4
   건조dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타to give a gummy solid
8. 8
   기타the resultant precipitate was collected
9. 9
   workup.ADDITIONHexane was added to the filtrate
10. 10
    기타once again the resultant precipitate was collected
11. 11
    기타dried in vacuo at 80° C.

실험 절차

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.

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