Diethyl Ether → HCID 57677338, compound

Participants

Reaction Steps

3-[6-(4-Amino-2-fluorophenoxy)pyrimidin-4-yl}-1-methyl-1-(1-methylpiperidin-4-yl)urea (50 mg) was dissolved in ethanol (1 ml), and then D-10-camphorsulfonic acid (62.3 mg) was added thereto, followed by stirring for 5 min. Phenylacetyl isothiocyanate (toluene solution, 0.355 M, 0.565 ml) was added thereto, followed by stirring further for 1 hr. The reaction mixture was partitioned between ethyl acetate (30 ml) and a saturated aqueous solution of sodium hydrogencarbonate (20 ml). The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (20 ml), water (20 ml) and brine (20 ml) in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate). Fractions containing the target compound were concentrated to give a residue, to which diethyl ether (0.5 ml)-hexane (2.0 ml) was then added to suspend a solid. The solid was filtered off and dried under aeration to provide the titled compound (12.4 mg, 16.8%) as pale yellow powder.

Provenance & Evidence