反応 #62259

反応方程式

Et3N

9-(2-hydroxy-4-phenyl-butyl)-2-pyridin-4-yl-3-(3-trifluoromethyl-phenyl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

DMSO

chloride

→

product

収率 66.4%

9-(2-Oxo-4-phenyl-butyl)-2-pyridin-4-yl-3-(3-trifluoromethyl-phenyl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one

収率 66.4%

溶媒

CH2Cl2

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   洗浄was washed with NaHCO3 (aq)
3. 3
   濃縮concentrated
4. 4
   洗浄The residue was eluted on silica gel with 0-5% (2N NH3-MeOH in CH2Cl2)

実験手順

A solution of DMSO (0.25 mL, 3.5 mmol) in CH2Cl2 (10 mL) at −78 C was treated with a solution of oxallyl chloride (2N in CH2Cl2, 0.8 mL, 1.6 mmol) dropwise. After stirring for 15 min, a solution of 9-(2-hydroxy-4-phenyl-butyl)-2-pyridin-4-yl-3-(3-trifluoromethyl-phenyl)-6,7,8,9-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (227 mg, 0.43 mmol) in CH2Cl2 (15 mL) was added. The mixture was stirred at −60 C for 15 min before a solution of Et3N (0.5 mL, 3.6 mmol) in CH2Cl2 (3 mL) was added. The reaction mixture was allowed to warm to room temperature overnight and was washed with NaHCO3 (aq). The organic layer was dired (Na2SO4), and concentrated. The residue was eluted on silica gel with 0-5% (2N NH3-MeOH in CH2Cl2) to afford the product as a light yellow solid (148 mg, 63%). M+1 519.

出典