Sodium borohydride → 5-Methyl-pyridine-2-sulfonic acid [2-[3-(2-hydroxy-ethoxy)-phenyl]-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide

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Reaction Steps

70 mg of {3-[4-methoxy-5-(2-methoxy-phenoxy)-6-(5-methyl-pyridine-2-sulfonylamino)-pyrimidin-2-yl]-phenoxy}-acetic acid methyl ester, product of example 2, were dissolved in a mixture of EtOH/THF (each 3 ml) on gentle warming and subsequently treated with 27.4 mg of CaCl2 and 18.7 mg of NaBH4 at RT. The reaction mixture was stirred at RT for 1.5 h until which time starting material was consumed according to TLC analysis (CH2Cl2/EtOAc: 3/1). The mixture was partitioned between 10% citric acid and EtOAc. The organic layer was dried over Na2SO4 and the solvent removed in vacuo. The residue was purified on a silica gel chromatography column (eluted with Me2Cl2EtOAc: 3/1). Combination of the purified fractions and evacuation in vacuo afforded 5-methyl-pyridine-2-sulfonic acid [2-[3-(2-hydroxy-ethoxy)-phenyl]-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide as a white solid. ISP mass spectrum, m/e 539.3 (M+1 calculated for C26H26N4O7S: 539).

Provenance & Evidence