Trimethylphosphine → 7-[(3aS,4R,6R,6aR)-6-(aminomethyl)-2,2-dimethylhexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Participants

Reaction Steps

To a solution of 7-[(3aS,4R,6R,6aR)-6-(azidomethyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine (527.5 mg, 1.6 mmol) in tetrahydrofuran (5 ml) under N2 was added 1M PMe3 in THF (3.2 ml, 3.2 mmol) and the reaction was stirred overnight. The reaction was quenched by the addition of H2O (1 ml), and stirred for 15 mins before being concentrated under reduced pressure. The crude material was purified by silica flash column chromatography, eluting with 2.5 to 20% 2M NH3 in MeOH in DCM to afford the title compound (376.9 mg, 78%) as a colorless gum: MS (ESI+) for C15H21N5O2 m/z 304.0 [M+H]+; LC purity 99% (ELS) (ret. time, solvent front); 1H NMR (500 MHz, MeOD) δ 7.26 (d, J=3.6 Hz, 1H), 8.07 (s, 1H), 6.61 (d, J=3.6 Hz, 1H), 4.97-5.06 (m, 1H), 4.90-4.97 (m, 1H), 4.55 (dd, J=7.3, 5.8 Hz, 1H), 2.82-2.91 (m, 1H), 2.70-2.81 (m, 1H), 2.39 (dt, J=12.6, 6.5 Hz, 1H), 2.26 (dt, J=12.6, 6.2 Hz, 1H), 1.93-2.10 (m, 1H), 1.54 (s, 3H), 1.25-1.35 (m, 3H).

Provenance & Evidence