Aluminium lithium hydride → HCID 178461453, compound

Participants

Reaction Steps

To a solution of cis-toluene-4-sulfonic acid 3-[8-amino-1-(4-phenoxyphenyl)-imidazo[1,5-a]pyrazin-3-yl]-cyclobutylmethyl ester (20.0 mg, 0.0370 mmol) in THF (1 mL) at −78° C. was added 1.0 M of LiAlH4 in THF (0.15 mL), and the mixture was allowed to warm to rt. Once the reaction was complete, a few drops of sat. NH4Cl was added to quench. The material was transferred to a separatory funnel, and extracted using DCM and sat. NaHCO3. The aqueous layer was washed twice with DCM, and the organic fractions were combined and concentrated in vacuo. The material was dissolved in minimal MeOH/DCM, and loaded onto a prep TLC plate, eluting with 2% (7N NH3 in MeOH)/DCM. The band containing the product was collected, and the material was filtered off by washing with 1:1 MeOH I DCM. The filtrate was concentrated in vacuo to afford the title compound. 1H NMR (400 MHz, CDCl3): δ=1.14 (d, J=6.3 Hz, 3H), 2.13-2.23 (m, 2H), 2.46-2.57 (m, 1H), 2.58-2.67 (m, 2H), 3.52-3.62 (m, 1H), 5.07 (br. s., 2H), 7.02-7.10 (m, 3H), 7.10-7.18 (m, 4H), 7.35-7.41 (m, 2H), 7.61-7.66 (m, 2H). MS (ES+): m/z 371.06 (100) [MH+]. HPLC: tR=2.67 min (polar—5 min).

Provenance & Evidence