2-Methyl-2-butene → 2-Fluoro-5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid

Participants

Reaction Steps

A solution of 2-fluoro-5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzaldehyde [120 mg, 0.31 mmol, Example 35(j)] and 2-methyl-2-butene (2.93 mL, 28 mmol) in t-butanol (4 mL) and THF (2 mL), is treated with a solution of sodium dihydrogen phosphate monohydrate (303 mg, 2.2 mmol) and sodium chlorite (0.28 g, 3.2 mmol) in water (2 mL) at room temperature. After 15 hours at 20° C., the mixture is concentrated and diluted with water. The mixture is adjusted to pH 3 and the resulting solid is filtered and dried to afford 2-fluoro-5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid. [118 mg, 96%, Example 20(a)]. LCMS: RT=2.38 minutes, MS: 398 (M+H). IC50=0.4 nM

Provenance & Evidence