Sodium Iodide → HCID 58710016, compound

Participants

Reaction Conditions

Reaction Steps

Into the suspension of 4-[4-(6-methoxypyridin-3-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (68.4 mg, 79% purity, 0.127 mmol) and NaI (19.1 mg, 0.127 mmol) in CH3CN (10 mL) was added trimethylsilyl chloride (1 M in THF, 0.765 mL, 0.765 mmol) at rt. The mixture was then heated at 80° C. in a flask under N2 for 48 h. After that time, the mixture was cooled at 0° C. and the aqueous solution (H2O, 8 mL) of NaHCO3 (159 mg) and NaS2O4.5H2O (318 mg) was added while stirring. The solid was filtered off and washed with water to obtain a brown-red solid. Boc2O (30.8 mg, 0.140 mmol), DMAP (17.1 mg, 0.140 mmol) and the above solid were dissolved in pyridine and the mixture was stirred at rt for 18 h. After that time, the mixture was concentrated in vacuo to obtain a green-yellow oil that was submitted for MS directed purification. One obtained the title compound as off-white solid. 1H NMR (DMSO-d6, 400 MHz): δ=1.44 (s, 9H), 2.46 (brs, 2H), 3.56 (t, 2H, J=5.4 Hz), 4.00 (brs, 2H), 6.38 (s, 1H), 6.40 (s, 1H), 6.67-7.70 (m, 1H), 8.02 (d, 1H, J=2.4 Hz), 8.20 (s, 1H), 9.06 (s, 1H), 11.40 (brs, 1H), 11.92 (s 1H). MS (ES+): m/z 409.05 (100) [MH+]. HPLC: tR=2.33 min (ZQ2000, polar—5 min).

Provenance & Evidence