Triphenylphosphine → HCID 178472386, compound

Participants

Reaction Steps

Into the THF (5 mL) solution of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (prepared according to: L. B. Townsend et al., J. Med. Chem. 1990, 33 (7), 1984-92) (140 mg, 0.500 mmol), 4-hydroxycyclohexanecarboxylic acid ethyl ester (104 mg, 0.600 mmol; Aldrich, cis/trans mixture), and PPh3 (263 mg, 1.00 mmol) was added DIAD (203 mg, 1.00 mmol) dropwise at 0° C. under N2 over 5 min. The reaction was then stirred at rt for 2 days. After that time, the solvent was evaporated, and the residue was purified by chromatography on silica gel, eluting with 200 mL of 5%, 10%, 20% and 30% EtOAc/hexane to obtain cis-4-(4-chloro-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-cyclohexanecarboxylic acid ethyl ester as a white solid, which was further purified by HPLC. 1H NMR (CDCl3, 400 MHz): δ=1.32 (t, 3H, J=7.2 Hz), 1.74-1.78 (m, 2 H), 1.88-1.98 (m, 4 H), 2.33-2.36 (m, 2 H), 2.75-2.77 (m, 1 H), 4.23 (q, 2 H, J=7.2 Hz), 4.73-4.81 (m, 1 H), 7.45 (s, 1 H), 8.60 (s, 1 H). MS (ES+): 433.9/435.9 [MH+]. HPLC: tR=4.0 min (polar—5 min).

Provenance & Evidence