Sodium Hydroxide → HCID 9998303, compound

To a 100-mL, round-bottomed flask containing 4-chloro-6-(4-trifluoromethyl-phenyl)pyrimidine, (Example 2(a), Method A), (0.20 g, 0.77 mmol) and 6-hydroxyindole (0.21 g, 1.5 mmol, Aldrich) in 1,4-dioxane (10 mL), was added NaOH (8.0 mL, 8.0 mmol, 1.0 N). The mixture was heated at reflux for 8 h, and after cooling to room temperature, the reaction mixture was concentrated in vacuum. EtOAc (30 mL) was added, and the organic layer was washed with brine (10 mL), water (15 mL), dried over Na2SO4, filtered, and concentrated in vacuum. After the product was purified by silica gel chromatography (5:1 hexanes/EtOAc), the residue was dissolved in acetone (3 mL). Water (4 mL) was then added dropwise to afford a white precipitate, which was collected by filtration, washed with water (0.5 mL), and dried under vacuum at 50° C. for 48 h to furnish the title compound. Mp: 206–209° C. MS (ESI, pos. ion) m/z: 356 (M+1); Anal. Calcd for C19H12F3N3O.(H2O)0.2: C, 63.58; H, 3.48; N, 11.71. Found: C, 63.82; H, 3.37; N, 11.61.

1. temperatureThe mixture was heated
2. temperatureat reflux for 8 h
3. concentrationthe reaction mixture was concentrated in vacuum
4. additionEtOAc (30 mL) was added
5. washthe organic layer was washed with brine (10 mL), water (15 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuum
9. customAfter the product was purified by silica gel chromatography (5:1 hexanes/EtOAc)
10. dissolutionthe residue was dissolved in acetone (3 mL)
11. additionWater (4 mL) was then added dropwise
12. customto afford a white precipitate, which
13. filtrationwas collected by filtration
14. washwashed with water (0.5 mL)
15. customdried under vacuum at 50° C. for 48 h

ORD record

ord-df14bdcdaac643f88f587b5a777cb333

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07144888B2