Ammonia → 2-Chloro-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine

To a solution of 2,4-dichloro-5-phenylpyrrolo[2,1-f][1,2,4]triazine (0.500 g, 1.89 mmol) in THF (5 mL), NH3 gas was bubbled at −20° C. for 15 min. The reaction mixture was stirred at RT for 1 h. The reaction mixture was concentrated under reduced pressure to remove THF and water (30 mL) was added to the resulting residue. The aqueous solution was extracted with EtOAc (3×100 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by CombiFlash (REDISEP®, silica gel, 40 g, 45% EtOAc/petroleum ether) to afford 2-chloro-5-phenylpyrrolo[2,1-f][1,2,4]triazin-4-amine (0.300 g, 64.8%). LCMS Condition B-81: retention time 2.14 min, [M+1]=245.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 5.98 (br s, 1H), 6.75 (d, J=2.4 Hz, 1H), 7.38-7.43 (m, 2H), 7.46-7.52 (m, 3H), 7.80 (d, J=2.4 Hz, 1H), 8.40 (br s, 1H).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. customto remove THF and water (30 mL)
3. additionwas added to the resulting residue
4. extractionThe aqueous solution was extracted with EtOAc (3×100 mL)
5. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by CombiFlash (REDISEP®, silica gel, 40 g, 45% EtOAc/petroleum ether)

ORD record

ord-fb1bab48f2cf49e4a8ecc4526e0304b6

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09050345B2