3-Fluoro-4-(4-pyridinylsulfanyl)aniline → 6-ethyl-N4-[3-fluoro-4-(4-pyridinylsulfanyl)phenyl]-2,4-pyrimidinediamine

Participants

Reaction Steps

2-Amino-4-chloro-6-ethylpyrimidine (Intermediate A8, 55.1 mg, 0.25 mmol) and Intermediate B7(39.4 mg, 0.25 mmol) were suspended in 0.01 M aqueous HCl (500 μL). The mixture was refluxed for 6 h. The reaction was cooled to room temperature and the solvent was evaporated by vacuum. The residue was purified by reversed phase chromatography on a YMC Pack-pro C18 column (trademark) eluting with acetonitrile/H2O (10:90-90:10 gradient). The compound was further purified by preparative TLC eluting with CH2Cl2-MeOH (90:10). Desired compound (2.9 mg, 0.0085 mmol; 34% yield); 1H NMR (Methanol-d4) 8.16 (dd, J=1.7, 4.7, 2H), 8.00-8.04 (m, 1H), 7.37 (m, 2H), 6.93 (dd, J=1.8, 4.9, 2H), 5.91 (s, 1H), 2.39 (q, J=7.7, 2H), 1.13 (t, J=7.5, 3H); ES MS [M+H]+=342; TLC (CH2Cl2-MeOH, 90:10); Rf=0.48.

Provenance & Evidence