تفاعل #969344

معادلة التفاعل

ethane-1,2-diamine

sodium hydroxide

N-(3-(5-(pyridin-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide

CF3CO2H

→

N-(3-(5-(pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   تركيزconcentrated in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in methanol (2 mL)
3. 3
   workup.STIRRINGThe resulting solution was stirred for 30 minutes at room temperature
4. 4
   تركيزbefore being concentrated in vacuo
5. 5
   استخلاصThe resulting solution was extracted with ethyl acetate (×3)
6. 6
   غسيلthe combined organic layers were washed with brine
7. 7
   تجفيفdried with anhydrous sodium sulfate
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated in vacuo
10. 10
    أخرىPurification of the crude product by reverse phase HPLC

الإجراء التجريبي

To a solution of N-(3-(5-(pyridin-2-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide (170 mg, 0.350 mmol) in dichloromethane (2.0 mL), was added CF3CO2H (2.0 mL). The resulting solution was stirred for 2 hours at 50° C. and then concentrated in vacuo. The residue was dissolved in methanol (2 mL), and ethane-1,2-diamine (42 mg, 0.70 mmol) and sodium hydroxide (98 mg, 1.6 mmol) were added. The resulting solution was stirred for 30 minutes at room temperature before being concentrated in vacuo. The resulting solution was extracted with ethyl acetate (×3) and the combined organic layers were washed with brine, dried with anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification of the crude product by reverse phase HPLC using an acetonitrile gradient in water with 0.5% TFA modifier afforded N-(3-(5-(pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)phenyl)methacrylamide as a white solid. LRMS (ESI) calc'd for C21H18N5O [M+H]+: 356, found 356. 1H NMR (400 MHz, CD3OD) δ 9.06 (s, 1H), 8.42 (d, J=5.6 Hz, 1H), 8.27 (s, 1H), 8.12-8.16 (m, 1H), 7.90 (s, 1H), 7.64-7.68 (m, 1H), 7.58 (d, J=8.0 Hz, 1H), 7.50 (d, J=6.8 Hz, 1H), 7.37-7.40 (m, 2H), 5.72 (s, 1H), 5.52 (s, 1H), 1.91 (s, 3H).

المصدر