Lawesson's reagent → HCID 68157800, compound

Participants

Reaction Conditions

Reaction Steps

2,4-Bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane (369 mg, 0.91 mmol) was added to (S)—N-[4-fluoro-2-(pyrimidin-2-ylamino)phenyl]-2-[9-(tetrahydropyran-2-yl)-9H-purin-6-ylamino]propionamide (109 mg, 0.23 mmol) in tetrahydrofuran (5.0 ml) and heated to 80° C. overnight. The reaction mixture was cooled and concentrated in vacuo. The residue was taken up in EtOAc/1M hydrochloric acid (aqueous), and the aqueous layer extracted with EtOAc three times. The aqueous layer was neutralised with sodium hydroxide (1M aqueous) and extracted with EtOAc (×3). The neutral organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The product was purified by chromatography (SiO2, 0-20% methanol in DCM) to yield 261 (35 mg, 41%). LCMS: RT 3.08 min [M+H]+ 376.0. 1H NMR (CDCl3, 400 MHz): δ 8.90 (2H, d, J=4.9 Hz), 8.02 (2H, s), 7.97 (1H, dd, J=9.8, 2.7 Hz), 7.60 (1H, dd, J=8.7, 5.0 Hz), 7.42 (1H, t, J=4.8 Hz), 7.08 (1H, td, J 9.0, 2.6 Hz), 6.52 (1H, br s), 1.83 (3H, d, J=6.8 Hz)

Provenance & Evidence