Reacción #88715

Ecuación de reacción

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

LiOH.H2O

→

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

Rendimiento 21.4%

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)-1-methyl-6-((6-methylpyridin-3-yl)oxy)-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (10 mg, 0.020 mmol) in THF (5 mL) and water (5 mL) was added LiOH.H2O (1.70 mg, 0.040 mmol). 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)-3-(3-hydroxypropyl)-1-methyl-6-((6-methylpyridin-3-yl)oxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (2 mg, 21.2% yield) as a white solid. 1H NMR (CDCl3) δ: 8.29 (s, 1H), 8.20 (d, J=2.4 Hz, 1H), 7.16-7.18 (m, 4H), 7.10 (d, J=8.6 Hz, 1H), 7.03 (s, 1H), 4.76 (s, 2H), 4.24 (t, J=6.2 Hz, 2H), 3.70 (s, 3H), 3.53-3.57 (m, 2H), 3.04 (t, J=7.0 Hz, 1H), 2.54 (s, 3H), 1.92-1.96 (m, 2H). LCMS: MH+ 467 and TR=1.903 min.

Fuente