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

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Reaction Conditions

Reaction Steps

[4-(2,4-Dimethyl-1H-pyrrol-3-yl)-pyrimidin-2-yl]-(4-fluoro-phenyl)-amine (80 mg, 0.28 mmol) was dissolved in THF (4 mL) and cooled to −60° C. N-Chlorosuccinimide (41 mg, 0.31 mmol) was dissolved in THF (2 mL) and added dropwise, keeping the internal temperature ≦−50° C. The mixture was stirred for 30 min with cooling then evaporated in vacuo. The residue was treated with H2O (10 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were washed (brine), dried (MgSO4), filtered, and evaporated in vacuo. The crude product was purified by SiO2 chromatography (heptane/EtOAc gradient elution) to afford the title compound (37 mg) as an orange solid after recrystallisation from iPr2O. M.p. 200–203° C. MS: [M+H]+=317.7 (C16H14ClFN4 requires 316.8). 1H-NMR (CDCl3) δ: 2.17 (s, 3H, CH3), 2.42 (s, 3H, CH3) 6.77 (d, 1H, J=5.9 Hz, pyrimidinyl-H), 7.02–7.06 (m, 3H, Ph-h, NH), 7.54–7.56 (m, 2H, Ph-H), 7.95 (br. s, 1H, NH), 8.25 (d, 1H, J=5.4 Hz, pyrimidinyl-H).

Provenance & Evidence