HCID 10400931, compound → HCID 10315728, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) solution of 3-[2-(methylthio)pyrimidin-4-yl]pyrazolo[1,5-a]pyridine-2-carbaldehyde (520 mg, 1.92 mmol) in tetrahydrofuran (40 mL) was added phenylmagnesium bromide (2.88 mL 1.0 M in tetrahydrofuran, 2.88 mmol). The reaction was warmed to 0° C. and stirred for 1 hour. The reaction mixture was then recooled to −78° C. and additional phenylmagnesium bromide (2.00 mL, 1.0 M in tetrahydrofuran, 2.00 mmol) was added and stirred at room temperature for 14 hours. The reaction was quenched with water and the resulting mixture was concentrated in vacuo to remove the excess tetrahydrofuran. The resulting aqueous mixture was extracted with dichloromethane. The organic layer was washed with water and dried over magnesium sulfate. Filtration and concentration, followed by flash chromatography (49:1 dichloromethane:methanol) provided {3-[2-(methylthio)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-2-yl}(phenyl)methanol (550 mg, 82%) as a white solid. Rf 0.31 (49:1 dichloromethane:methanol); 1H NMR (CDCl3) δ 8.52 (d, 1H), 8.40 (d, 1H), 7.87 (d, 1H), 7.43–7.13 (m, 7H), 6.93 (t, 1H), 6.21 (s, 1H), 2.60 (s, 3H); MS m/349 (M+1).

Provenance & Evidence