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

Temperature

50 °C

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 stalling material was in solution and was then cooled in an ice-water bath. 1M 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 it. 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) 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 stalling material
2. temperaturewas then cooled in an ice-water bath
3. temperatureto warm to it
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-9f0b7e7db52446f28d45e0f4d8b2d428

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08133995B2