تفاعل #88711

معادلة التفاعل

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

LiOH.H2O

→

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

المردود 18.6%

المذيبات

THF

water

EA

water

ظروف التفاعل

المعالجة

1. 1
   تجفيفThe organic layer was dried over Na2SO4
2. 2
   تركيزconcentrated to a residue which
3. 3
   أخرىwas purified by Prep HPLC

الإجراء التجريبي

To a solution of 3-(5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-6-((5-(trifluoromethyl)pyridin-3-yl)oxy)-1,2-dihydropyrido[2,3-d]pyrimidin-3(4H)-yl)propyl formate (45.3 mg, 0.083 mmol) in THF (5 mL) and water (5 mL) was added LiOH.H2O (6.93 mg, 0.165 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 5-(4-chlorobenzyl)-3-(3-hydroxypropyl)-1-methyl-6-((5-(trifluoromethyl)pyridin-3-yl)oxy)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (8 mg, 18.6% yield) as a white solid. 1H NMR (CDCl3) δ: 8.82 (s, 1H), 8.35 (s, 1H), 8.26 (d, J=3.0 Hz, 1H), 7.53 (d, J=3.0 Hz, 1H), 7.12 (d, J=8.4 Hz, 2H), 7.01 (d, J=8.3 Hz, 2H), 4.26-4.20 (m, 4H), 3.71 (s, 3H), 3.58-3.54 (m, 2H), 2.97 (brd s, 1H), 1.96-1.90 (m, 2H). LCMS: MH+ 521 and TR=2.765 min.

المصدر