Triethylamine → 3,8-Diphenylimidazo[1,2-d][1,2,4]triazin-2-ol

Temperature

0 °C

To a solution of 6-phenyl-[1,2,4]triazin-5-ylamine (1.1 g, 6.4 mmol) and triethylamine (891 μl, 6.4 mmol) in anhydrous 1,2-dichloroethane (75 ml) under an atmosphere of nitrogen was added dropwise 2-chloro-2-phenylacetyl chloride (1.01 ml, 6.4 mmol). The reaction mixture was stirred at 0° C. for 90 min, then triethylamine (891 μl, 6.4 mmol) was added, and the resulting mixture heated under reflux for 30 min. The cooled reaction mixture was partitioned between CH2Cl2 (100 ml) and water (100 ml). The organic layer was separated, dried over MgSO4 and evaporated in vacuo. The solid residue was triturated with a 1:1 mixture of CH2Cl2 and MeOH (10 ml), filtered and dried to give 780 mg (2.7 mmol, 42%) of 3,8-diphenylimidazo[1,2-d][1,2,4]triazin-2-ol as a pale yellow solid. δH (360 MHz; DMSO-d6) 7.41 (1H, t, J 7.3 and 7.2, aromatic), 7.50-7.63 (5H, m, aromatics), 7.82 (2H, d, J 7.8, aromatics), 8.57 (2H, m, aromatics), 9.65 (1H, s, imidazotriazine H5), 11.72 (1H, br s, OH); m/z (ES+) 289 (M++H, 100%).

1. temperaturethe resulting mixture heated
2. temperatureunder reflux for 30 min
3. customThe cooled reaction mixture
4. customwas partitioned between CH2Cl2 (100 ml) and water (100 ml)
5. customThe organic layer was separated
6. dry with materialdried over MgSO4
7. customevaporated in vacuo
8. customThe solid residue was triturated with a 1:1 mixture of CH2Cl2 and MeOH (10 ml)
9. filtrationfiltered
10. customdried

ORD record

ord-2d5163358aa24522a644e870509da177

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608062B1