Methyl acetoacetate → Methyl 2-(thien-2-yl)-4-(2-chloro-4-fluorophenyl)-6-methyl-1,4-dihyropyrimidin-5-carboxylate

2.164 mmol of 2-thienylformamidine hydrochloride (Schaefer F. C., Peters G. A., et al, J. Org. Chem.; 1961, 26(2): 412-418), 2.164 mmol of 2-chloro-4-fluorobenzaldehyde, 2.164 mmol of methyl acetoacetate and 2.2 mmol of sodium acetate in 10 ml of anhydrous ethanol was reacted under reflux for 20 hours and concentrated. Ethyl acetate and water were added to the reaction, and the phases were separated. The ethyl acetate layer was dried over anhydrous sodium sulfate and separated by a column chromatography to give 0.22 g of a yellow crystal (yield: 30%); 1H-NMR (400 MHz, CDCl3) δ 2.55 (3H, s, CH3); 3.62 (3H, s, CH3); 6.00 (1H, s, CH); 6.89-6.94 (1H, m, ArH); 7.03-7.05 (1H, dd, J1=4.80 Hz, J2=3.60 Hz, ArH); 7.11-7.14 (1H, m, ArH); 7.26-7.30 (1H, m, ArH); 7.33-7.34 (1H, d, J2=3.60 Hz, ArH); 7.44-7.45 (1H, d, J1=4.80 Hz ArH); MS (HREI) 344.0448 (M+).

1. temperatureunder reflux for 20 hours
2. concentrationconcentrated
3. additionEthyl acetate and water were added to the reaction
4. customthe phases were separated
5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
6. customseparated by a column chromatography

ORD 기록

ord-5af85200ea7c4f7b9c883564a93cab19

출처 데이터셋

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08106196B2