1,2-Dimethoxyethane → HCID 16123802, compound

Participants

Reaction Conditions

Reaction Steps

Pd(dppf) dichloromethane adduct (115 mg, 0.141 mmol) was added to a suspension of 6-bromo-2-{[4-(4-ethylpiperazin-1-yl)phenyl]amino}-4-methyl-8-(1-methylethyl)pyrido[2,3-d]pyrimidin-7(8H)-one (341 mg, 0.703 mmol), 2-thiophene boronic acid (99 mg, 0.77 mmol), and triethylamine (245 μL, 1.76 mmol) in 10:1 DME:water (6.6 mL). The reaction was heated to 100° C. After 24 h, the reaction was cooled to room temperature, diluted with water (50 mL) and filtered though a Celite plug and concentrated in vacuo. The residue was purified on reverse phase HPLC (25 mM ammonium acetate:acetonitrile, 30-80% gradient). The fractions containing product were collected and lyophilized to give 2-{[4-(4-Ethylpiperazin-1-yl)phenyl]amino}-4-methyl-8-(1-methylethyl)-6-(2-thienyl)pyrido[2,3-d]pyrimidin-7(8H)-one. (23 mg, 7% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3): δ 8.08 (s, 1H), 7.63 (bd, J=3.2 Hz, 1H), 7.51 (m, 2H), 7.40 (bd, J=4.4 Hz, 1H), 7.11 (m, 2H), 6.97 (m, 2H), 5.90 (sept, 1H), 3.23 (m, 4H), 2.68 (s, 3H), 2.65 (m, 4H), 2.50 (q, J=7.2 Hz, 2H), 1.63 (d, J=6.8 Hz, 6H), 1.15 (t, J=7.2 Hz, 3H); MS (EI) for C27H32N6OS: 489.1 (MH+).

Provenance & Evidence