Phosphorus oxychloride → 4-chloro-N-(3,5-dimethylphenyl)pyrimidin-2-amine
反応式
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[NH:15][C:14](=O)[CH:13]=[CH:12][N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.O=P(Cl)(Cl)[Cl:19]>>[Cl:19][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([NH:9][C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)[N:15]=1参加物
3
反応条件
- 温度
- 100 °C
実験手順
2-(3,5-Dimethyl-phenylamino)-3H-pyrimidin-4-one (2.01 g, 9.34 mmol) was dissolved in POCl3 (8.70 ml, 93.4 mmol) and the mixture was heated to 100° C. in a round bottom flask equipped with a reflux condenser and a drying tube. After 5 hours the reaction was cooled to room temperature and concentrated in vacuo. The residue was quenched by the addition of sat NaHCO3 (aq) and was extracted 3× with DCM. The combined organic extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography (dissolved sample in DCM, eluted with 85:15 hexane/EtOAc) to afford 4-chloro-N-(3,5-dimethylphenyl)pyrimidin-2-amine (4-3).