Reaktion #88717

Reaktionsgleichung

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

Ausbeute 34.7%

Lösungsmittel

THF

water

EA

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TrocknenThe organic layer was dried over Na2SO4
2. 2
   Filtrationfiltered
3. 3
   Einengenconcentrated to a residue which
4. 4
   Sonstigewas purified by Prep HPLC

Vorschrift

To a solution of 3-(5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-6-(6-(trifluoromethyl)pyridin-3-yloxy)-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (20 mg, 0.036 mmol) in THF (2 mL) and water (2 mL) was added LiOH.H2O (4.6 mg, 0.109 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-(6-(trifluoromethyl)pyridin-3-yloxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (6.5 mg, 34.2% yield) as a white solid. 1H NMR (CDCl3) δ: 8.44 (d, J=3.2 Hz, 1H), 8.21 (s, 1H), 7.84 (d, J=3.2 Hz, 1H), 7.57 (s, 1H), 7.28-7.24 (overlap with CDCl3, 2H), 7.12 (t, J=8.8 Hz, 2H), 4.25 (t, J=6.0 Hz, 2H), 4.08 (s, 2H), 3.74 (s, 3H), 3.61-3.54 (m, 2H), 2.93 (brd s, 1H), 1.97-1.90 (m, 2H). LCMS: MH+ 521 and TR=2.625 min.

Quelle