1-((4-methoxyphenyl)methyl)-1H-pyrazol-5-amine → HCID 59490360, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (E)-6-((dimethylamino)methylene)-2-(methylamino)-7,8-dihydroquinazolin-5(6H)-one (2.8 g, 12 mmol) and 1-(4-methoxybenzyl)-1H-pyrazol-5-amine (2.69 g, 13 mmol) was added trifluoroacetic (1 mL). The reaction mixture was heated at 100° C. for 16 hours. The reaction was then cooled to room temperature followed by addition of isopropanol (20 mL). The reaction mixture was the stirred for 30 minutes and the supernatant decanted. The residue was dried under reduced pressure. The crude product was purified using flash column chromatography (SiO2, gradient from 100 hexanes to 15% EtOAc in hexanes) to give desired product (1.0 g, 22%) as solid. 1H NMR (CDCl3, 400 MHz): δ 9.32 (s, 1H), 7.90 (s, 1H), 7.75 (s, 1H), 7.40 (d, J=8.0 Hz, 2H), 6.82 (d, J=8.0 Hz, 2H), 5.52-5.48 (m, 1H), 5.62 (s, 2H), 3.76 (s, 3H), 3.18-3.04 (m, 5H), 3.0-2.88 (m, 2H); LCMS [M+H]: 373.

Provenance & Evidence