Diisopropylethylamine → 8-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-yl-(3,5-dimethyl-phenyl)-amine

Participants

Reaction Steps

To a solution of 3,5-dimethylisothiocyanate (200 mg, 1.2 mmol) in dichloro-methane and N,N-dimethylformamide (1:1) (5.0 mL) were added 1,2-diamino-3-chloro-pyrazinium mesitylenate (0.59 g, 0.0017 mol) and diisopropylethylamine (791 mg, 6.1 mmol). The reaction mixture was stirred for 1 hour. EDCl (93 mg, 5 mmol) was added and the solution stirred for 2 hours at room temperature before being concentrated to dryness. The residue was taken up in water and stirred for 5 minutes and the solid precipitated was filtered, washed with water, dried to get the product as a light brown solid (0.25 g, 75%). TLC: pet ether/ethyl acetate (6/4) Rf-0.4. LCMS (method A): mass found (M+H+, 274.0), Rt (min): 4.47 area % 98.0 (max), 98.47 (254 nm); 1H NMR (400 MHz, DMSO-d6): δ 9.99 (s, 1H), 8.95 (d, J=4.28 Hz, 1H), 7.91 (d, J=4.32 Hz, 1H), 7.28 (s, 2H), 6.58 (s, 1H), 2.24 (s, 6H).

Provenance & Evidence