Tetrahydrofuran → 4-Aminopyrrolo[2,1-f][1,2,4]triazine-6-carbaldehyde

To a solution of THF (200 mL) was added 4-aminopyrrolo[2,1-f][1,2,4]triazine-6-carbonitrile (1.00 g, 6.28 mmol). The solution was heated until all starting material was in solution and was then cooled in an ice-water bath. 1 M Diisobutylaluminum hydride in THF (50.3 mL, 50.3 mmol) was then added to the solution which was stirred for 1 h. EtOAc was added to the solution and it was then allowed to warm to rt. Wet silica gel was carefully pipetted into the solution, and the reaction mixture was heated to 50° C. for 30 min, filtered through Celite, and washed with excess EtOAc. The solution was transferred to a separatory funnel and washed with water. The organic layer was collected, dried (MgSO4), filtered, and concentrated to dryness yielding 0.92 g of yellow solid (5.69 mmol, yield 91%). 1H-NMR (DMSO-d6) δ 9.91 (s, 1H) 7.92 (d, J=1.7 Hz, 1H), 8.14 (d, J=35.3 Hz, 2H), 7.89 (s, 1H), 7.30 (d, J=1.8 Hz, 1H); MS [M+H]+=163.3; LCMS RT=1.07 min.

1. temperatureThe solution was heated until all starting material
2. temperaturewas then cooled in an ice-water bath
3. temperaturethe reaction mixture was heated to 50° C. for 30 min
4. filtrationfiltered through Celite
5. washwashed with excess EtOAc
6. customThe solution was transferred to a separatory funnel
7. washwashed with water
8. customThe organic layer was collected
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated to dryness

ORD record

ord-8942384aea3b4dfa84787eff97900528

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829185B2