Dichloromethane → HCID 24963249, compound

Participants

Reaction Steps

To a mixture of (S)-3-(2,3-dihydroxypropyl)-6-fluoro-5-(2-fluoro-4-((trimethylsilyl)ethynyl)phenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione 21A in THF (3 mL) was added 1M solution of TBAF (0.14 mL, 0.14 mmol, 1.75 eq). The reaction mixture was stirred at ambient temperature for 1 hour. The solvent was removed under vacuum and the residue was purified by flash chromatography with 2:8 MeOH:DCM to yield the desired product (S)-3-(2,3-dihydroxypropyl)-5-(4-ethynyl-2-fluorophenylamino)-6-fluoro-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (example 21) as an off-white solid (10 mg, 30% yield). 1H NMR (400 MHz, MeOD) δ ppm 3.54 (s, 1 H) 3.60 (d, J=5.05 Hz, 2 H) 3.72 (s, 3 H) 3.75-3.83 (m, 1 H) 3.93-4.00 (m, 1 H) 4.41 (dd, J=13.52, 2.91 Hz, 1 H) 7.11 (td, J=8.15, 5.68 Hz, 1 H) 7.21-7.29 (m, 2 H) 8.40 (s, 1 H). [M+H] calc'd for C19H16F2N4O4, 403; found, 403.

Provenance & Evidence