4-Aminopyrimidine → 4-(4-cyano-2-methoxyphenyl)-N-(pyrimidin-4-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of perfluorophenyl 4-(4-cyano-2-methoxyphenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonate (180 mg, 0.351 mmol) and 4-amino pyrimidine (50 mg, 0.527 mmol) in THF (5 mL) was added LiHMDS (1M in THF, 0.7 mL, 0.703 mmol) at −78° C. The reaction mixture was stirred at same temperature for 5 minutes and at 0° C. for 1 h. After completion, reaction mixture was quenched with 2-3 drops of acetic acid and concentrated under reduced pressure. The crude mass was purified by prep purification to obtain 4-(4-cyano-2-methoxyphenyl)-N-(pyrimidin-4-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (13 mg, 11.3%) as a white solid. m/z (ESI) 423.0 (M+H)+. 1H NMR (400 MHz, DMSO) δ 11.88 (s, 1H), 8.64 (s, 1H), 8.36 (d, J=5.8 Hz, 1H), 7.65 (s, 1H), 7.55-7.43 (m, 2H), 7.35-7.15 (m, 2H), 7.00 (d, J=5.9 Hz, 1H), 6.34 (d, J=8.6 Hz, 1H), 4.30 (t, J=4.0 Hz, 2H), 3.81 (s, 3H), 3.67-3.65 (m, 2H).

Provenance & Evidence