2,4-Dichloro-1,3,5-triazine → 6-Bromo-2-(4-chloro-1,3,5-triazin-2-yl)-1,2,3,4-tetrahydroisoquinoline

Temperature

0 °C

2,4-Dichloro-1,3,5-triazine (2.01 g, 12.7 mmol) was dissolved in 10 mL of dry DMF and the solution was cooled to 0° C. To this solution was added N,N-diisopropylethylamine, (6.65 mL, 38.2 mmol) and 6-bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride (3.26 g, 12.7 mmol). The resulting reaction mixture was stirred at 0° C. to RT for 1.5 h. The reaction mixture was quenched with water (10 mL) and extracted with EtOAc. The organics were dried with MgSO4, filtered and concentrated under reduced pressure. The crude material obtained was purified with medium pressure silica gel chromatography using gradient eluent, 0-40% EtOAc in hexanes to afford 6-bromo-2-(4-chloro-1,3,5-triazin-2-yl)-1,2,3,4-tetrahydroisoquinoline (1.90 g, 46% yield) as white solid.

1. customThe resulting reaction mixture
2. customThe reaction mixture was quenched with water (10 mL)
3. extractionextracted with EtOAc
4. dry with materialThe organics were dried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe crude material obtained
8. customwas purified with medium pressure silica gel chromatography

ORD record

ord-897a3673e1c94125895df27b8f3ed6ab

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09334269B2