Chloride → 7H-Pyrrolo[2,3-d]pyrimidine-5-carboxylic acid, 4-[5-[(2-methyl-1-oxo-2-propen-1-yl)amino]-3-pyridinyl]-, ethyl ester

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Reaction Steps

To ethyl 4-(5-aminopyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (59 mg, 0.14 mmol) in DCM (1.0 mL) was added Hunig's base (0.060 mL, 0.34 mmol) at 0° C. Methacyloyl chloride (0.015 mL, 0.15 mmol) was then added dropwise and the reaction was allowed to warm to room temperature. After being stirred for 17 hours at room temperature, MeOH was added to quench the reaction and the solution was concentrated in vacuo. The crude reaction was purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. The products were collected and lyophilized to afford a colorless solid. LRMS (ESI) calc'd for C18H18N5O3 [M+H]+: 352, found 352. 1H NMR (600 MHz, DMSO-D6) δ 13.17 (s, 1H), 10.22 (s, 1H), 9.04 (s, 1H), 9.02 (d, 1H, J=1.7 Hz), 8.55 (s, 1H), 8.50 (m, 1H), 8.45 (m, 1H), 5.93 (s, 1H), 5.65 (s, 1H), 3.99 (q, 2H, J=7.2 Hz), 2.01 (s, 3H), 1.00 (t, 3H, J=7.2 Hz).

Provenance & Evidence