反応 #158534

反応方程式

2,4-dichloro-5-fluoropyrimidine

3-aminophenol

HCl

→

N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine

N2,N4-Bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine

溶媒

H2O

MeOH

water

反応条件

後処理

1. 1
   抽出Upon saturation with sodium chloride it was extracted with ethyl acetate (3×20 mL)
2. 2
   乾燥dried over anhydrous sodium sulfate and solvent
3. 3
   その他was removed
4. 4
   ろ過The resulting residue was filtered through a pad of silica gel (200-400 mesh)

実験手順

A mixture of 2,4-dichloro-5-fluoropyrimidine (0.0167 g, 0.1 mmol) and 3-aminophenol (0.033 g, 0.3 mmol) in MeOH: H2O (1.8:0.2 mL; v/v) was shaken in a sealed tube at 100° C. for 24 h (or 80° C. for 3 days), cooled to room temperature, diluted with water (15 mL), acidified with 2N HCl (pH>2). Upon saturation with sodium chloride it was extracted with ethyl acetate (3×20 mL), dried over anhydrous sodium sulfate and solvent was removed. The resulting residue was filtered through a pad of silica gel (200-400 mesh) using CH2Cl2->1>10% MeOH in CH2Cl2 to obtain the desired N2,N4-bis(3-hydroxyphenyl)-5-fluoro-2,4-pyrimidinediamine (R921218). If the reaction scale is large enough, solid of the resulting product can be isolated by filtration. 1H NMR (CDCl3): δ 7.73 (d, 1H, J=5.1 Hz), 7.12-6.90 (m, 6H), 6.64 (dd, 1H, J=1.8 and 8.1 Hz), 6.53 (dd, 1H, J=1.2 and 5.7 Hz); LCMS: ret. time: 16.12 min.; purity: 100%; MS (m/e): 313 (MH+).

出典