Dimethyl Sulfoxide → 4-Nitro-6-{2-[4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethoxy}-pyrimidin-5-ylamine

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Reaction Conditions

Reaction Steps

2-[4-(4-Trifluoromethylpyridin-2-yloxy)-phenyl]-ethanol (product from Step 1; 400 mg, 1.4 mmol) was dissolved in DMSO (10 mL), treated with 95% NaH (36 mg, 1.5 mmol) and the mixture was warmed to 50-60° C. to produce a clear solution. Upon cooling the mixture was treated with 4-amino-5-nitro-6-chloropyrimidine (260 mg, 1.5 mmol) and heated at 45° C. for 6 h. After cooling the mixture was poured into H2O (60 mL) and the precipitate was collected by suction filtration, washed with H2O and air-dried on the filter: 1H NMR (300 MHz, CDCl3) δ 8.39 (s, 1H), 8.33 (s, 1H), 8.18 (s, 1H), 7.38 (m, 2H), 7.15 (m, 4H), 4.69 (t, J=6.8 Hz, 2H), 3.15 (t, 6.6 Hz, 2H). This material was used in the next step without further purification.

Provenance & Evidence