反応 #88637

反応方程式

3-(5-(4-chlorobenzyl)-1,7-dimethyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3 (2H,4H,5H)-yl)propyl acetate

LiOH.H2O

→

5-(4-chlorobenzyl)-3-(3-hydroxypropyl)-1,7-dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione

収率 41.9%

溶媒

THF

water

DCM

water

反応条件

後処理

1. 1
   乾燥The organic layer was dried over Na2SO4
2. 2
   濃縮concentrated to a residue which
3. 3
   その他was purified by Prep HPLC

実験手順

To a solution of 3-(5-(4-chlorobenzyl)-1,7-dimethyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3 (2H,4H,5H)-yl)propyl acetate (40 mg, 0.099 mmol) in THF (5 mL) and water (5 mL) was added LiOH.H2O (4.74 mg, 0.198 mmol). The reaction was stirred at RT for 30 min then diluted with DCM (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 5-(4-chlorobenzyl)-3-(3-hydroxypropyl)-1,7-dimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (15 mg, 41.9% yield) as a white solid. 1H NMR (DMSO-d6) δ: 7.38 (d, J=8.4 Hz, 2H), 7.26 (s, 1H), 7.22 (d, J=8.4 Hz, 2H), 5.45 (s, 2H), 4.44 (t, J=5.3 Hz, 1H), 3.95-3.82 (m, 2H), 3.56 (s, 3H), 3.45-3.39 (m, 2H), 2.26 (s, 3H), 1.73-1.58 (m, 2H). LCMS: MH+ 362 and TR=2.343 min.

出典