Reacción #88699

Ecuación de reacción

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

LiOH.H2O

→

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

Rendimiento 63.1%

Disolventes

THF

water

EA

water

Condiciones de reacción

Tratamiento posterior

1. 1
   SecadoThe organic layer was dried over Na2SO4
2. 2
   Filtraciónfiltered
3. 3
   Concentraciónconcentrated to a residue which
4. 4
   Otrowas purified by Prep HPLC

Procedimiento

To a solution of 3-(5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-6-(pyridin-3-yloxy)-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (10.3 mg, 0.021 mmol) in THF (5 mL) and water (5 mL), was added LiOH.H2O (1.80 mg, 0.042 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, filtered and concentrated to a residue which was purified by Prep HPLC to give 5-(4-chlorobenzyl)-3-(3-hydroxypropyl)-1-methyl-6-(pyridin-3-yloxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (6 mg, 61.8% yield) as a white solid. 1H NMR (CDCl3) δ: 8.39 (d, J=4.6 Hz, 1H), 8.33 (d, J=4.5 Hz, 2H), 7.24 (d, J=4.7 Hz, 1H), 7.17 (s, 4H), 7.10 (dd, J=8.4, 1.6 Hz, 1H), 4.75 (s, 2H), 4.24 (t, J=6.1 Hz, 2H), 3.71 (s, 3H), 3.62-3.49 (m, 2H), 2.99 (t, J=6.8 Hz, 1H), 2.00-1.84 (m, 2H). LCMS: MH+ 453 and TR=1.963 min.

Fuente