Morpholine → 3-[5-Amino-6-(morpholin-4-ylmethyl)pyrazin-2-yl]-N-(phenylmethyl)benzamiide

Participants

Reaction Steps

3-(5-Amino-6-formylpyrazin-2-yl)-N-benzylbenzamide (1.27 g, 3.83 mmol) was dissolved in dichloroethane (30 mL) at 0° C. Morpholine (400 mg, 4.6 mmol), and NaBH(OAc)3 (2.03 g, 9.58 mmol) were added and the reaction was stirred at room temperature for 20 h. The reaction mixture was diluted with saturated sodium carbonate and extracted 3× with ethyl acetate. The combined ethyl acetate layers were dried over sodium sulfate, filtered, and concentrated iii vacuo to afford the product (1.41 g, 88% yield). 1H NMR (400 MHz, d4-CD3OD): δ 8.60 (s, 1H), 8.47 (t, 1H), 8.12 (m, 1H), 7.84 (m, 1H), 7.55 (t, 1H), 7.31-7.89 (m, 4H), 7.23-7.26 (m, 1H), 4.61 (s, 2H), 4.43 (s, 2H), 3.32-4.16 (m, 8H). MS (EI) for C23H25N5O2: 404 (MH+).

Provenance & Evidence