Cyclohexane → HCID 57636113, compound

Participants

Reaction Steps

A mixture of 5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-thiophene-2-carbaldehyde [200 mg, 0.54 mmol, Example 8(b)] in MeOH (5 mL) and THF (5 mL) at 0° C. is treated with sodium borohydride (41 mg, 1.08 mmol). The mixture is stirred at ambient temperature for 1 hour and concentrated by rotary evaporator to remove the solvent. The residual solid is dissolved in water and the solution is extracted with ethyl acetate. The organic extract is dried over magnesium sulfate, filtered and concentrated to afford a solid which is subjected to flash column chromatography on silica gel eluting with a mixture of EtOAc and cyclohexane) to afford (5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-thiophen-2-yl)-methanol [75 mg, 37%, Example 9(a)] as a solid. LCMS: RT=6.09 minutes; MS: 372 (M+H). IC50=0.55 nM

Provenance & Evidence