4-(3-Dimethylamino-acryloyl)-3,4-dimethyl-5-methylsulfanyl-4,5-dihydro-thiophene-2-carbonitrile → 3-Methyl-5-methylsulfanyl-4-(2-phenylamino-pyrimidin-4-yl)-thiophene-2-carbonitrile

Participants

Reaction Steps

4-(3-Dimethylamino-acryloyl)-3,4-dimethyl-5-methylsulfanyl-4,5-dihydro-thiophene-2-carbonitrile (0.2 mmol) was combined with N-phenyl-guanidine (0.2 mmol) in acetonitrile (0.25 mL) and the resulting mixture heated at reflux for 24 hours. The reaction mixture was diluted with methanol (3mL) and the resulting slurry filtered and the solid was washed with methanol (2 mL) then dried under nitrogen to afford IIa-37. M+H=507.1, HPLC: Rt=6.196 minutes, 1H NMR (500 Mz, DMSO) 9.77(s, 1H), 8.25(d, 1H, J=5.3 Hz), 7.69(s, 1H), 7.48(m, 2H), 7.48(m, 4H), 7.41(t, 2H, J=7.3 Hz), 7.34(t, 1H, J=7.2 Hz), 7.25(d, 1H, J=8.3 Hz), 7.21 (t, 1H, J=8.0 Hz), 6.67(d, 1H, J=6.7 Hz), 6.01(d, 1H, J=5.3 Hz), 5.11(s, 2H), 3.32(s, 3H, CH3), 2.68(s, 3H, CH3).

Provenance & Evidence