Water → HCID 178449086, compound

Participants

Reaction Steps

Trifluoroacetic Acid (20 ml, 300 mmol) added to a mixture of Water (2 ml, 100 mmol) and 7-((3aS,4R,6R,6aR)-6-(((3-(2-(5-(tert-butyl)-1H-benzo[d]imidazol-2-yl)ethyl)cyclobutyl)(isobutyl)amino)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-N-(2,4-dimethoxybenzyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.9 g, 1 mmol) at RT. The reaction was stirred overnight and Triethylsilane (0.38 ml, 2.4 mmol) was added. The volatiles were removed in vacuo and resulting residue was taken up in MeOH (15 ml), 500 mgs of K2CO3 and 8 drops H2O were added and reaction stirred at RT for 1 hour. The mixture was filtered and filter cake washed with 10 ml MeOH. The filtrate was concentrated and the resulting residue purified by flash chromatography (DCM/7N NH3 in MeOH 90:10) to yield the desired product (0.274 g) as an off white foam. MS (ESI+) for C23H47N7O2 m/z 574.6 [M+H]+; MS (ESI−) for C33H45N7O2 m/z 572.4 [M−H]−; HPLC purity >86% (ret. time, 2.918 min.) 1H NMR (400 MHz, d4-MeOH) δH 8.078 (s, 1H), 7.497 (s, 1H), 7.416-7.396 (m, 1H), 7.305-7.284 (m, 1H), 7.216-7.200 (m, 1H), 6.621-6.612 (d, J=3.6 Hz, 1H), 4.368-4.334 (m, 1H), 3.930-3.894 (m, 1H), 2.934-2.918 (m, 1H), 2.866-2.797 (m, 2H), 2.652-2.583 (m, 1H), 2.444-2.361 (m, 2H), 2.287-2.199 (m, 2H), 2.166-2.119 (m, 3.5H (contains methine of trans isomer)), 2.048-2.012 (m, 1H), 1.921-1.748 (m, 3.5H (contains methine of cis isomer)), 1.622-1.494 (m, 2H), 1.380 (s, 9H), 1.269-1.252 (m, 1H), 0.932-0.879 (m, 6H).

Provenance & Evidence