p-Toluenesulfonic acid monohydrate → HCID 90041903, compound

Participants

Reaction Conditions

Reaction Steps

p-Toluenesulfonic acid monohydrate (75 mg, 0.395 mmol) was added to a solution of 2-chloro-4-(trifluoromethyl)pyrimidine (36 mg, 0.198 mmol) and 5-(morpholin-4-ylmethyl)biphenyl-3-amine (53 mg, 0.198 mmol) in dioxane (1.98 mL) and heated to 80° C. for 14 hours, then allowed to cool to room temperature. The mixture was diluted with ethyl acetate (30 mL) and washed with saturate aqueous NaHCO3 (30 mL) and 1:1 water: brine (2×30 mL). The organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (thyl acetate/hexanes) provided N-[5-(morpholin-4-ylmethyl)biphenyl-3-yl]-4-(trifluoromethyl)pyrimidin-2-amine. MS ESI calc'd. for C22H22F3N4O [M+H]+ 415, found 415. 1H NMR (400 MHz, CDCl3): δ 8.67 (d, J=4.9 Hz, 1H); 7.90 (s, 1H); 7.66 (d, J=7.7 Hz, 2H); 7.58 (s, 1H); 7.51-7.42 (m, 3H); 7.39 (t, J=7.4 Hz, 1H); 7.33 (s, 1H); 7.06 (d, J=4.9 Hz, 1H); 3.76 (t, J=4.5 Hz, 4H); 3.61 (s, 2H); 2.54 (t, J=4.2 Hz, 4H).

Provenance & Evidence