반응 #68958

반응 방정식

Sodium methoxide

5-(8-bromoisoquinolin-3-ylamino)pyrazine-2-carbonitrile

→

title compound

수율 6.0%

5-(8-methoxyisoquinolin-3-ylamino)pyrazine-2-carbonitrile

수율 6.0%

용매

DMF

반응 조건

후처리

1. 1
   기타The three reaction mixtures
2. 2
   기타The combined reaction mixtures
3. 3
   기타were partitioned between ethyl acetate and water
4. 4
   추출the aqueous layer re-extracted with more ethyl acetate
5. 5
   세척The combined organic phases were washed with brine
6. 6
   건조dried (Na2SO4)
7. 7
   농축concentrated in vacuo
8. 8
   기타Purification by preparative HPLC

실험 절차

Sodium methoxide (55 mg, 0.10 mmol) was added to a pre-stirred mixture of 5-(8-bromoisoquinolin-3-ylamino)pyrazine-2-carbonitrile (33 mg, 0.10 mmol) and copper iodide (19 mg, 0.10 mmol) in DMF in triplicate. The three reaction mixtures were heated at 140° C. for 30 minutes, 110° C. for 18 hours, and 120° C. for 10 minutes, respectively. The combined reaction mixtures were partitioned between ethyl acetate and water and the aqueous layer re-extracted with more ethyl acetate. The combined organic phases were washed with brine, dried (Na2SO4), and concentrated in vacuo. Purification by preparative HPLC gave the title compound (1.7 mg, 0.006 mmol, 2%). 1H NMR (DMSO, 400 MHz) δ 9.33 (s, 1H), 8.81 (d, 1H, J=1.3 Hz), 8.71 (d, 1H, J=1.3 Hz), 8.43 (s, 1H), 7.64 (t, 1H, J=8.1 Hz), 7.43 (d, 1H, J=8.3 Hz), 6.97 (d, 1H, J=7.6 Hz), 4.01 (s, 3H). LCMS (2) Rt=2.87 min, m/z (ESI+) 278 (MH+).

출처