Acetic Acid → HCID 11660848, compound

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Reaction Steps

To a solution of 4-(3-oxo-propyl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile (610 mg) in methanol (8 ml) was added 1-(s)-methyl-2-methoxyethylamine (0.85 mL), acetic acid (0.5 mL), and followed by sodium triacetoxyborohydride (0.82 g). The mixture was stirred at room temperature for 4 hours, then diluted with sodium bicarbonate aqueous solution (5%, 50 ml). The mixture was extracted with ethyl acetate (50 ml plus 3×20 ml). Combined organic layer was dried over sodium sulphate, filtered, solvent removed under vacuum. Residue was columned on silica gel using DCM-MeOH (20:1) as eluant to give 4-[3-(1-(s)-methyl-2-methoxyethylamino)-propyl]-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile (250 mg). The above neutral product was dissolved in DCM and then HCl (1M in ether, 1 ml) added, 4-[3-(1-(s)-methyl-2-methoxyethylamino)-propyl]-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile HCl salt was collected by filtration (180 mg). 1H NMR (MeOD): δ 8.50 (s, 1H), 8.48 (d, 1H), 8.27 (s, 1H), 7.90 (d, 1H), 7.79 (t, 1H), 3.68 (m, 1H), 3.48 (m, 2H), 3.43 (s, 3H), 3.17 (m, 2H), 3.10 (t, 2H), 2.25 (m, 2H), 1.36 (d, 3H). MS m/z 379.5 (M+1), 80%.

Provenance & Evidence