Sodium borohydride → 1-(5-(4-Amino-6-methyl-1,3,5-triazin-2-YL)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-YL)ethanol

Participants

Reaction Steps

1-(5-(4-Amino-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanone (250 mg, 0.677 mmol) was dissolved in THF (1.35 mL), sodium borohydride (128 mg, 3.38 mmol) was added, and the resulting mixture was stirred at ambient temperature for 2 h. The reaction mixture was then quenched with water and added to a separatory funnel. The reaction mixture was then partitioned between EtOAc (100 mL) and ammonium chloride (saturated, aqueous). The organic layer was separated, washed 2 times with 75 mL of ammonium chloride (saturated, aqueous), dried over sodium sulfate, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0% to 5% (2 M ammonia in MeOH)/DCM) gave the title compound (40% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 11.90 (s, 1H) 8.87 (s, 1H) 8.34 (d, J=2.15 Hz, 1H) 8.20-8.30 (m, 1H) 8.05 (d, J=1.76 Hz, 1H) 5.41 (br. s., 2H) 4.95 (q, J=6.52 Hz, 1H) 4.03 (s, 3H) 2.57 (s, 3H) 1.83 (br. s., 1H) 1.58 (br. s., 3H). m/z (ESI, +ve ion) 372.0 (M+H)+.

Provenance & Evidence