Formaldehyde → Ammonia

Participants

Reaction Steps

Add sodium triacetoxyborohydride and aqueous formaldehyde (37%w/w, to a solution of (S)-2-Butyl-10-(3-phenethyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene (0.50 g, 1.1 mmol) in dichloroethane (12 mL) and stir. After 5 hours, dilute with a saturated aqueous solution of sodium bicarbonate, and separate the layers. Extract the aqueous layer with dichloromethane (3×), combine organics, and dry (sodium sulfate), filter, and concentrate under reduced pressure to an oil (0.24 g). Purify the oil by flash chromatography, eluting with a gradient of a 5% solution of 2M ammonia in methanol, in dichloromethane (0–100% over 30 minutes), and then with a 5% solution of 2M ammonia in methanol, in dichloromethane to give the title compound (0.19 g): Mass spectrum (APCI+, m/e): 460 (M+1); 1H NMR (300 MHz, CDCl3), δ (ppm): 7.39–7.11 (m, 5H), 7.11–6.95 (m, 2H), 6.94–6.81 (m, 1H), 6.69–6.57 (m, 1H), 5.01 (s, 1H), 4.40–3.93 (br. m, 1H), 3.34–3.16 (m, 1H), 3.08–2.92 (m, 1H), 2.93–2.40 (m, 7H), 2.40–2.23 (m, 4H), 2.06–1.51 (m, 4H), 1.38 (d, 2H, J=7.1 Hz), 0.90 (t, 3H, J=7.1 Hz).

Provenance & Evidence