تفاعل #3275

معادلة التفاعل

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

NaH

Methyl chloroacetate

→

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

المردود 61.0%

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىresulting in a clear solution
2. 2
   درجة الحرارةthe solution was heated at 50° C. for 20 minutes
3. 3
   درجة الحرارةcooled to room temperature
4. 4
   أخرىThe resulting precipitate was removed by filtration
5. 5
   غسيلwashed with water
6. 6
   استخلاصThe aqueous filtrate was extracted with ethyl acetate
7. 7
   تجفيفthe organic layer was dried over magnesium sulfate
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated
10. 10
    أخرىpurified by flash chromatography
11. 11
    غسيلeluting with a gradient of 1:1 hexane

الإجراء التجريبي

To a suspension of NaH (60% in mineral oil, 38 mg) in 6 mL of dimethylformamide was added 2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7(8H)-one (203 mg, 0.66 mmol). The mixture was heated at 50° C. for 40 minutes resulting in a clear solution. Methyl chloroacetate (90 μL, 1.03 mmol) was added, and the solution was heated at 50° C. for 20 minutes, then cooled to room temperature and poured onto 30 mL of ice water. The resulting precipitate was removed by filtration and washed with water. The aqueous filtrate was extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate, filtered, and concentrated. The solids were combined and purified by flash chromatography, eluting with a gradient of 1:1 hexane:ethyl acetate to all ethyl acetate to provide 152 mg (61%) of [2-amino-6-(2,6-dichlorophenyl)-7-oxo-7H-pyrido[2,3-d]pyrimidin-8-yl]-acetic acid methyl ester; mp 188°-190° C.

المصدر