Reacción #88707

Ecuación de reacción

3-(5-(4-chlorobenzyl)-6-((5-chloropyridin-3-yl)oxy)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate

LiOH.H2O

→

5-(4-chlorobenzyl)-6-((5-chloropyridin-3-yl)oxy)-3-(3-hydroxypropyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Rendimiento 21.2%

Disolventes

THF

water

EA

water

Condiciones de reacción

Tratamiento posterior

1. 1
   SecadoThe organic layer was dried over Na2SO4
2. 2
   Concentraciónconcentrated to a residue which
3. 3
   Otrowas purified by Prep HPLC

Procedimiento

To a solution of 3-(5-(4-chlorobenzyl)-6-((5-chloropyridin-3-yl)oxy)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (40 mg, 0.078 mmol) in THF (6 mL) and water (6 mL) was added LiOH.H2O (6.51 mg, 0.156 mmol) at 20° C. The reaction was stirred at RT for 30 min. then diluted with EA (10 mL) and water (10 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 5-(4-chlorobenzyl)-6-((5-chloropyridin-3-yl)oxy)-3-(3-hydroxypropyl)-1-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (8 mg, 21.2% yield) as a white solid. 1H NMR (CDCl3) δ: 8.52 (s, 1H), 8.39 (d, J=3.0 Hz, 1H), 8.10 (s, 1H), 7.71 (d, J=3.0 Hz, 1H), 7.17 (d, J=8.5 Hz, 2H), 7.11 (d, J=8.4 Hz, 2H), 4.24 (t, J=6.1 Hz, 2H), 4.19 (s, 2H), 3.72 (s, 3H), 3.57 (d, J=5.0 Hz, 2H), 2.99 (s, 1H), 2.00-1.85 (m, 2H). LCMS MH+ 487 and TR=2.436 min.

Fuente