Triethyl orthoacetate → 3-(3-chloro-4-morpholinophenyl)-2,6-dimethylpyrimidin-4(3H)-one
Reaction equation
[NH2:1]/[C:2](/[CH3:20])=[CH:3]\[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[C:9]([Cl:19])[CH:8]=1)=[O:5].[C:21](OCC)(OCC)(OCC)[CH3:22]>>[Cl:19][C:9]1[CH:8]=[C:7]([N:6]2[C:4](=[O:5])[CH:3]=[C:2]([CH3:20])[N:1]=[C:21]2[CH3:22])[CH:12]=[CH:11][C:10]=1[N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1Participants
3
Conditions
- Temperature
- 150 °C
Procedure
A mixture of (Z)-3-amino-N-(3-chloro-4-morpholinophenyl)but-2-enamide (2.0 g, 6.76 mmol) and triethyl orthoacetate (20 mL) was stirred at 150° C. for 12 h. The mixture was cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a pale yellow solid (1.63 g, 76%). The compound was characterized by the following spectroscopic data: