Water → HCID 66589241, compound

Participants

Reaction Steps

To a solution of (S)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-[1-(4-fluorophenyl)ethyl]pyrimidine-2,4,5-triamine (Method 8; 0.04 g, 0.1 mmol) in aqueous acetic acid (5%, 3 ml) was slowly added an aqueous NaNO2 solution (0.008 g, 0.1 mmol, 1 ml H2O). The reaction was allowed to stir for an additional 5 minutes, treated with water (10 ml), and extracted with DCM (3×25 ml). The combined organic layer was washed with saturated NaHCO3 solution (50 ml), dried, filtered, and concentrated. The resulting solid was purified by column chromatography (DCM:MeOH=15:1) to give the title compound (0.015 g, 40%). NMR (400 MHz, CD3OD) 9.05 (s, 1H), 7.44-7.41 (m, 2H), 7.03-6.99 (m, 2H), 6.23 (s, 1H), 5.16-5.07 (m, 1H), 2.03-2.00 (m, 1H), 1.55 (d, J=6.8 Hz, 3H), 1.11-1.09 (m, 2H), 0.85-0.80 (m, 2H). MS: Calcd.: 364; Found: [M+H]+ 365.

Provenance & Evidence