Reaktion #88796

Reaktionsgleichung

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

LiOH.H2O

→

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

Ausbeute 21.2%

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-(trifluoromethoxy)phenoxy)-1,2-dihydro pyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (50 mg, 0.098 mmol) in THF (2 mL) and water (2 mL was added LiOH.H2O (8.2 mg, 0.196 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 3-(3-hydroxypropyl)-5-isopentyl-1-methyl-6-(3-(trifluoromethoxy)phenoxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (10 mg, 20.0% yield) as a white solid. 1H NMR (DMSO-d6) δ: 8.57 (s, 1H), 7.49 (t, J=8.8 Hz, 1H), 7.11 (d, J=8.0 Hz, 1H), 6.98-6.95 (m, 2H), 4.51 (t, J=5.6 Hz, 1H), 4.02-3.97 (m, 2H), 3.58 (s, 3H), 3.50-3.45 (m, 2H), 3.15-3.10 (m, 2H), 1.77-1.70 (m, 2H), 1.54-1.50 (m, 1H), 1.32-1.23 (m, 2H), 0.79 (d, J=6.8 Hz, 6H). LCMS: MH+ 482 and TR=3.447 min.

Quelle