Dimethylformamide → 4-chloro-1,6-diphenylpyrimidine-2(1H)-one

Oxalyl chloride (3.1 g, 24.4 mmol) was added to a mixture of N,N-dimethylformamide (1.8 g, 24.6 mmol) in dichloromethane (30 ml) at −5° C. to 0° C. under stirring. After the completion of addition the reaction temperature was allowed to reach 20° C. to 25° C. 1,6-Diphenyluracil (4.0 g, 15.2 mmol) was added in portions to the resulted suspension for 2.5 hrs. The reaction mixture was heated to reflux for 4 hours under stirring and continued stirring for 12 hours at room temperature. The reaction mass was poured onto sodium hydroxide solution (150 ml, 0.25 N) and collected the dichloromethane layer. The dichloromethane layer was washed with hydrochloric acid (200 ml, 0.025N), water and saturated sodium chloride solution successively. The organic extract was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the title compound (1.5 g, 35%, HPLC purity 99.8%), mp: 141-143° C.

1. additionAfter the completion of addition the reaction temperature
2. customto reach 20° C. to 25° C
3. temperatureThe reaction mixture was heated
4. temperatureto reflux for 4 hours
5. stirringunder stirring
6. stirringcontinued stirring for 12 hours at room temperature
7. additionThe reaction mass was poured onto sodium hydroxide solution (150 ml, 0.25 N)
8. customcollected the dichloromethane layer
9. washThe dichloromethane layer was washed with hydrochloric acid (200 ml, 0.025N), water and saturated sodium chloride solution successively
10. extractionThe organic extract
11. dry with materialwas dried over anhydrous sodium sulphate
12. concentrationconcentrated under reduced pressure

ORDレコード

ord-94f8aa3ec04643b483392ccf2219087b

出典データセット

uspto-grants-2008_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07317014B2