2-Methoxyethanol → 4-(2,4-dimethyl-5-nitro-1H-pyrrol-3-yl)-N-(4-fluorophenyl)pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

3-Dimethylamino-1-(2,4-dimethyl-5-nitro-1H-pyrrol-3-yl)-propenone (110 mg, 0.46 mmol), 4-fluorophenyl guanidine nitrate (150 mg, 0.7 mmol), and K2CO3 (193 mg, 1.4 mmol) were partially dissolved in 2-methoxyethanol and heated at 120° C. for 18 h. The mixture was concentrated in vacuo and purified by SiO2 chromatography (heptane/EtOAc gradient elution). The crude product was triturated in iPr2O to afford the title compound (22 mg) as a pale orange solid. M.p. 166.3–170.1° C. MS: [M+H]+=329.3 (C16H14FN5O2 requires 327.3). 1H-NMR (DMSO-d6) δ: 2.49 (s, 3H, CH3), 2.59 (s, 3H, CH3), 6.73 (d, 1H, J=5.1 Hz, pyrimidinyl-H), 7.04 (t, 2H, J=8.8 Hz, Ph-H), 7.07 (br. s, 1H, NH), 7.55–7.58 (m, 2H, Ph-H), 8.44 (d, 1H, J=5.1 Hz, pyrimidinyl-H), 9.40 (br. s, 1H, NH).

Provenance & Evidence