Phosphorus oxychloride → HCID 59655729, compound

Temperature

80 °C

To a stirred slurry of 7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one (I-2A-1a; 30.0 g, 80.8 mmol) in toluene (400 ml) at room temperature was added diisopropylethylamine (30.3 ml, 173 mmol) and then POCl3 (15.9 ml, 168 mmol) over 10 minutes. The mixture was heated at 80° C. for 5 hours, cooled to room temperature, and then slowly quenched by slow addition to half saturated brine (300 ml). The biphasic mixture was flitered through Celite® to remove the brown solids that formed on quench. The organic layer was separated and washed with saturated aqueous NaHCO3 (200 ml) and then brine (200 ml). The organic solution was concentrated, in vacuo, to ½ volume and then filtered through a cotton plug. The solution was further concentrated to ¼ volume, at which point, a yellow solid began to precipitate. Hexane (300 ml) was then added and stirred for 1 hour. The solids were collected on a sintered glass funnel and dried, in vacuo, to afford the desired product I-2A-1b (22.3 g, 71%) as a dark-yellow solid: +APcI MS (M+1) 389.1; 1H NMR (400 MHz, CD2Cl2) δ 7.50-7.39 (m, 6H), 7.28 (d, J=8.7 Hz, 2H), 2.73 (s, 3H).

1. temperaturecooled to room temperature
2. customslowly quenched by slow addition to half saturated brine (300 ml)
3. customto remove the brown solids that
4. customformed
5. customon quench
6. customThe organic layer was separated
7. washwashed with saturated aqueous NaHCO3 (200 ml)
8. concentrationThe organic solution was concentrated, in vacuo
9. filtrationfiltered through a cotton plug
10. concentrationThe solution was further concentrated
11. customto precipitate
12. additionHexane (300 ml) was then added
13. customThe solids were collected on a sintered glass funnel
14. customdried, in vacuo

ORD record

ord-7b41f193862e4e07bd51bd891edd34f0

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07329658B2