Reacción #88448

Ecuación de reacción

3-(5-(4-chlorobenzyl)-6-(3-chlorophenoxy)-1-methyl-2,4-dioxo-1,2-dihydro pyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate

LiOH.H2O

→

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

Rendimiento 26.4%

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)-6-(3-chlorophenoxy)-1-methyl-2,4-dioxo-1,2-dihydro pyrido[3,4-d]pyrimidin-3(4H)-yl)propyl formate (20 mg, 0.0389 mmol) in THF (2 mL) and water (2 mL) was added LiOH.H2O (3.2 mg, 0.078 mmol). The reaction was stirred at RT for 15 min, then diluted with EA (20 mL) and water (20 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-(3-chlorophenoxy)-3-(3-hydroxypropyl)-1-methylpyrido[3,4-d]pyrimidine-2,4(1H,3H)-dione (5 mg, 26% yield) as a white solid. 1H NMR (CDCl3) δ: 8.20 (s, 1H), 7.74 (dd, J=11.1, 9.8, 5.7 Hz, 2H), 7.32 (t, J=8.1 Hz, 1H), 7.23-7.16 (m, 3H), 7.03 (t, J=2.1 Hz, 1H), 6.90 (dd, J=8.2, 1.5 Hz, 1H), 4.82 (s, 2H), 4.24 (t, J=6.2 Hz, 2H), 3.60 (d, J=13.0 Hz, 3H), 3.56 (d, J=5.6 Hz, 2H), 2.87 (s, 1H), 1.99-1.84 (m, 2H). LCMS: MH+ 486 and TR=3.024 min

Fuente