Water → HCID 67816524, compound

Participants

Reaction Steps

7-[(3aS,4R,6R,6aR)-6-(Azidomethyl)-2,2-dimethyl-hexahydrocyclopenta[d][1,3]dioxol-4-yl]-N-cyclopropyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (4.683 g, 12.55 mmol) was dissolved in THF (23 ml) and trimethylphosphane (1M in THF) (25 ml, 25.1 mmol) was added at r.t. under N2 and the reaction stirred overnight. Water (2.25 ml) was added and the reaction was left for 15 mins. The solvents were removed in vacuo to give the crude product. The product was purified by silica flash column chromatography using between 100% DCM to 20% 2M NH3 in MeOH:80% DCM as eluent to give the product as pale yellow viscous oil (3.964 g, 92%): MS (ESI+) for C18H25N5O2 m/z 344.5 [M+H]+, 366.0 [M+Na]+; LC purity 100% (UV), 100% (ELS) (ret. time, 0.21 and 0.44 min); 1H NMR (500 MHz, CDCl3) δ 8.18 (s, 1H), 7.25 (d, J=3.63 Hz, 1H), 6.70 (br. s., 1H), 5.03 (dt, J=12.06, 6.27 Hz, 1H), 4.92-4.99 (m, 1H), 4.55 (dd, J=7.25, 5.99 Hz, 1H), 2.82-2.93 (m, 2H), 2.72-2.82 (m, 1H), 2.39 (dt, J=12.65, 6.52 Hz, 1H), 2.23-2.28 (m, 1H), 2.03 (q, J=12.14 Hz, 1H), 1.56 (s, 3H), 1.31 (s, 3H), 0.82-0.93 (m, 2H), 0.60-0.71 (m, 2H).

Provenance & Evidence