Reaktion #88703

Reaktionsgleichung

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

LiOH.H2O

→

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

Ausbeute 13.3%

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 TLC
4. 4
   Wascheneluted with PE/EA (1:1)

Vorschrift

To a solution of 3-(5-(4-chlorobenzyl)-6-((5-fluoropyridin-3-yl)oxy)-1-methyl-2,4-dioxo-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (32 mg, 0.064 mmol) in THF (6 mL) and water (6 mL) was added LiOH.H2O (5.38 mg, 0.128 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 TLC eluted with PE/EA (1:1) and then Prep HPLC to give 5-(4-chlorobenzyl)-6-((5-fluoropyridin-3-yl)oxy)-3-(3-hydroxypropyl)-1-methyl pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (4 mg, 13.2% yield) as a white solid. 1H NMR (CDCl3) δ: 8.47-8.35 (m, 2H), 8.03 (s, 1H), 7.76 (d, J=3.0 Hz, 1H), 7.18 (d, J=8.4 Hz, 2H), 7.12 (d, J=8.4 Hz, 2H), 4.24 (t, J=6.1 Hz, 2H), 4.06 (s, 2H), 3.73 (s, 3H), 3.57 (t, J=5.6 Hz, 2H), 2.01-1.88 (m, 2H). LCMS: MH+ 471 and TR=2.246 min.

Quelle