3-Aminopropionitrile → (+/-)-3-[1-(5-Benzyl-3-methyl-4-oxo-4,5-dihydro-isoxazolo[5,4-d]pyrimidin-6-yl)-propylamino]-propionitrile

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Reaction Steps

A solution of the compound of Example 1 Step 4 (2.0 g, 5.5 mmol) in EtOH (50 mL) treated 3-amino-propionitrile (1.55 g, 22.1 mmol) and stirred at reflux for 6 h. The mixture was cooled to room temperature and concentrated under vacuum. The resulting material was purified by preparative reverse-phase HPLC (CH3OH/H2O) on a YMC S10 ODS 50×500 mm column to afford the desired product as a yellow glass (1.2 g, 62%); 1H NMR (CD3OD): δ 7.38 (m, 5H), 5.65 (d, J=16.5 Hz, 1H), 5.30 (d, J=16.5 Hz, 1H), 4.65 (t, J=6.0 Hz, 1H), δ 3.15 (m, 1H), 2.72 (m, 1H), 2.70 (t, J=7.5 Hz, 2H), 2.59 (s, 3H), 1.92 (m, 2H), 0.89 (t, J=7.5 Hz, 3H)); LC/MS (ESI): 352 (M+H)+.

Provenance & Evidence