4-Aminopyrimidine → HCID 89761876, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of perfluorophenyl 4-(4-chloro-2-cyanophenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonate (370 mg, 0.717 mmol) and 4-amino pyrimidine (102 mg, 1.07 mmol) in THF (5 mL) was added LiHMDS (1M in THF, 1.43 mL, 1.43 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 5 min and at 0° C. for 1 h. After completion, the reaction mixture was quenched with 2-3 drops of acetic acid and concentrated under reduced pressure. The crude mass was purified by combi flash column chromatography (12 g column; elution: 2.5% methanol in DCM) to provide 4-(4-chloro-2-cyanophenyl)-N-(pyrimidin-4-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (48 mg, 15.6%) as an off-white solid. 1H NMR (400 MHz, DMSO) δ 11.87 (s, 1H), 8.66 (s, 1H), 8.40 (s, 1H) 8.15 (d, J=2.4 Hz, 1H), 7.86 (dd, J=8.7, 2.5 Hz, 1H), 7.60 (d, J=8.8 Hz, 1H), 7.12-6.96 (m, 1H), 7.43-7.24 (m, 2H), 6.56 (d, J=8.6 Hz, 1H), 4.34 (s, 2H), 3.77 (s, 2H); LCMS (ESI) m/z; 427.95 (M+H).

Provenance & Evidence