2-Methoxyethanol → 2-{4-[4-(Acetyl)piperazin-1-yl]anilino}-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)-5-fluoropyrimidine

Participants

Reaction Steps

A solution of (2Z)-3-(dimethylamino)-2-fluoro-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one (Method 14; 6.0 g, 25 mmol) and N-[4-(4-acetylpiperazin-1-yl)phenyl]guanidine bicarbonate salt (Method 2; 12.12 g, 37.5 mmol) in 2-methoxyethanol (90 ml) was heated under reflux for 18 hrs. The reaction mixture was evaporated under reduced pressure and the title compound was isolated by MPLC on silica gel (3% MeOH/DCM). It was obtained as a crisp foam on evaporation. Yield=8.9 g (81%). NMR: 1.36 (d, 6H), 2.03 (s, 3H), [2.5 (s, 3H) under DMSO signal], 2.98 (m, 2H), 3.08 (m, 2H), 3.57 (m, 4H), 5.44 (septuplet, 1H), 6.90 (d, 2H), 7.34 (d, 1H), 7.42 (d, 2H), 8.44 (d, 1H), 9.24 (s, 1H); m/z 438.

Provenance & Evidence