Hydrazine hydrate (1:1) → [4-(5-Amino-2,4-dimethyl-1H-pyrrol-3-yl)-pyrimidin-2-yl]-(4-fluoro-phenyl)-amine

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Reaction Steps

[4-(2,4-Dimethyl-5-nitro-1H-pyrrol-3-yl)-pyrimidin-2-yl]-(4-fluoro-phenyl)-amine (45 mg, 0.14 mmol) was dissolved in EtOH (3 mL) and 10% Pd(C) catalyst (10 mg) was added, followed by hydrazine hydrate (48 μL of a 55% w/w aq solution, 0.84 mmol). The mixture was heated at reflux for 18 h. The cooled mixture was filtered through a pad of Celite filter aid and the filtrate was evaporated in vacuo. The residue was purified by SiO2 chromatography (20:1 EtOAc/2 M ammonia in MeOH) to afford the title compound (14 mg) as a yellow solid. M.p. 227–231° C. MS: [M+H]+=397.8 (C16H16FN5 requires 297.3). 1H-NMR (CDCl3) δ: 1.98 (s, 3H, CH3), 2.37 (s, 3H, CH3), 4.86 (br. s, 2H, NH2), 6.65 (d, 1H, J=4.9 Hz, pyrimidinyl-H), 7.03 (t, 2H, J=8.3 Hz, Ph-H), 7.49 (br. s, 2H, NH), 7.58–7.61 (m, 2H, Ph-H), 8.53 (d, 1H, J=4.9 Hz, pyrimidinyl-H).

Provenance & Evidence