반응 #46256

반응 방정식

6-aminomethyl-4H-[1,2,4]triazin-5-one

N,N′-diisopropylethylamine

cyclobutanecarbonyl chloride

→

title compound

Cyclobutanecarboxylic acid (5-oxo-4,5-dihydro-[1,2,4]triazin-6-ylmethyl)-amide

용매

N,N′-dimethylforamide

pyridine

반응 조건

후처리

1. 1
   기타The reaction mixture was quenched with H2O (2 mL)
2. 2
   농축concentrated in vacuo
3. 3
   기타purified by chromatography on silica gel [eluting with 5% MeOH in CH2Cl2 (200 mL)→10% MeOH in CH2Cl2 (800 mL)]

실험 절차

To a solution of 6-aminomethyl-4H-[1,2,4]triazin-5-one (500 mg, 3.96 mmol) and N,N′-diisopropylethylamine (DIEA) (0.829 mL, 4.76 mmol) in anhydrous N,N′-dimethylforamide (DMF) (20 mL) and anhydrous pyridine (2 mL) was dropwise charged with cyclobutanecarbonyl chloride (0.451 mL, 3.96 mmol) at 0° C. then warmed to rt and stirred for an additional 1.5 h. The reaction mixture was quenched with H2O (2 mL), concentrated in vacuo, and purified by chromatography on silica gel [eluting with 5% MeOH in CH2Cl2 (200 mL)→10% MeOH in CH2Cl2 (800 mL)], affording the title compound; 1H NMR (DMSO-d6, 400 MHz) δ 1.7-1.82 (m, 1H), 1.70-1.92 (m, 1H); 1.97-2.07 (m, 2H); 2.07-2.19 (m, 2H); 3.55-3.67 (m, 1H); 4.19 (d, 2H); 7.97 (brt, J=5.6 Hz, 1H); 8.67 (s, 1H); MS (ES+): m/z 209.25 (100) [MH+], HPLC: tR=1.56 min (MicromassZQ, polar—5 min).

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