Ammonium Chloride → HCID 11404298, compound

Participants

Reaction Steps

To 2-methyl-4,5-dihydro-thiazolo[4,5-h]quinazolin-8-ylamine (100 mg, 0.46 mmol) in pyridine (3 mL) was added 3-butenyl chloroformate (68 μL, 74 mg, 0.55 mmol). The mixture was stirred at room temperature for 16 h. Ammonium chloride solution was added (50 mL) and the product was extracted with CH2Cl2 (3×50 mL). The organic extracts were combined, dried, filtered, and concentrated under vacuum to give a yellow solid. Crystallisation from EtOAc afforded the pure title product as yellow crystals (122 mg, 84%): mp 204° C. (dec). Anal. RP-HPLC: tR 14.1 min (0-60% MeCN, purity 100%). 1H-NMR (CDCl3): δ 8.36 (s, 1H, Py-H), 7.49 (brs, 1H, NH), 5.90-5.75 (m, 1H, CH), 5.19-5.07 (m, 2H, CH2), 4.27 (t, 2H, J 6.6, CH2), 3.06 (m, 4H, CH2—CH2), 2.77 (s, 3H, CH3), 2.45 (m, 2H, CH2). MS (ESI+): m/z 339.00 (M+Na)+.

Provenance & Evidence