Reaktion #88791

Reaktionsgleichung

3-(5-isopentyl-1-methyl-2,4-dioxo-6-(3-(trifluoromethyl)phenoxy)-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate

LiOH.H2O

→

3-(3-hydroxypropyl)-5-isopentyl-1-methyl-6-(3-(trifluoromethyl)phenoxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Ausbeute 46.5%

Lösungsmittel

THF

water

EA

water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

To a solution of 3-(5-isopentyl-1-methyl-2,4-dioxo-6-(3-(trifluoromethyl)phenoxy)-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (30 mg, 0.060 mmol) in THF (4 mL) and water (4 mL)) was added LiOH.H2O (5.10 mg, 0.12 mmol). The reaction was stirred at RT for 15 min then diluted with EA (5 mL) and water (5 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 3-(3-hydroxypropyl)-5-isopentyl-1-methyl-6-(3-(trifluoromethyl)phenoxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (13 mg, 45.9% yield) as a white solid. 1H NMR (DMSO-d6) δ: 8.58 (s, 1H), 7.61 (t, J=7.8 Hz, 1H), 7.48 (d, J=7.6 Hz, 1H), 7.26 (d, J=8.6 Hz, 2H), 4.50 (t, J=5.2 Hz, 1H), 4.09-3.93 (m, 2H), 3.58 (s, 3H), 3.48 (q, J=6.3 Hz, 2H), 3.19-3.06 (m, 2H), 1.75 (dd, J=14.0, 6.8 Hz, 2H), 1.51 (dd, J=13.0, 6.6 Hz, 1H), 1.29 (dd, J=15.3, 7.2 Hz, 2H), 0.79 (d, J=6.6 Hz, 6H). LCMS: MH+ 466 and TR=3.373 min.

Quelle