Dimethyl Sulfide → [5,6-Difluoro-4-(4-fluorophenyl)-2-oxo-3-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]acetaldehyde

To a −78° C. solution of 2.6 g (6.495 mmol) 4-allyl-5,6-difluoro-4-(4-fluorophenyl)-3-(2,2,2-trifluoroethyl)-3,4-dihydroquinazolin-2(1H)-one in 25 ml MeOH was bubbled ozone. After 15 mins at −78° C., the ozone was removed and the reaction mixture was quenched with 4.8 mL (64.946 mmol) dimethyl sulfide. After stirring at room temperature overnight, the reaction mixture was diluted with EtOAc and washed three times with water and brine. The organic layer was dried over NaSO4, filtered and concentrated in vacuo. Afforded [5,6-difluoro-4-(4-fluorophenyl)-2-oxo-3-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]acetaldehyde. 1H NMR (CDCl3, 400 MHz) δ 9.79 (s, 1H, O═CH); 8.61 (br s, 1H, ArNHC═O); 7.38-7.27 (m, 2H, ArH); 7.15-7.03 (m, 3H, ArH); 6.57-6.53 (m, 1H, ArH); 4.08 (m, 1H, C); 3.72 (dd, 1H, J=17.4 Hz, CH2C═O); 3.50 (dd, 1H J=1.28 Hz, 17.58 Hz, CH2C═O); 3.32 (m, 1H, CH2C═O). ES MS+1=403.1.

1. customthe ozone was removed
2. washwashed three times with water and brine
3. dry with materialThe organic layer was dried over NaSO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo

ORD 기록

ord-74eae65960864069a122f877c9fbc7db

출처 데이터셋

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07745452B2