Sodium Bicarbonate → HCID 58169359, compound

Participants

Reaction Steps

The mixture of (E)-3-(4-(1-acetyl-5-cyclopropyl-1H-pyrazol-3-ylamino)-2-phenylpyrimidin-5-yl)allyl acetate (80 mg, 0.192 mmol, 1.0 equiv.) and NaHCO3 (144 mg, 1.724 mmol, 9.0 eqiv.) in EtOH (20 mL) was stirred at room temperature for 24 h. The reaction mixture was filtered, the filtrate was concentrated. The residue was diluted with EtOAc and washed with water, brine, dried (Na2SO4), and filtered. The filtrate was concentrated and purified by silica gel chromatography (EtOAc/MeOH 20:1) to afford (E)-3-(4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-phenylpyrimidin-5-yl)allyl acetate (Compound 81) (8 mg, 11.1%). LC-MS (m/z): 376.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 0.72-0.73 (m, 2H), 0.96-0.98 (m, 2H), 1.91-1.98 (m, 1H), 2.07 (s, 3H), 4.70 (d, J=5.6 Hz, 2H), 6.35 (d, J=15.2 Hz, 1H), 6.46 (s, 1H), 7.10 (d, J=15.2 Hz, 1H), 7.47-7.49 (m, 3H), 8.29-8.30 (m, 2H), 8.54 (s, 1H), 9.29 (s, 1H), 12.16 (s, 1H).

Provenance & Evidence