Dichloromethane → HCID 118208792, compound

Participants

Reaction Steps

N-(3-Bromo-5-methylphenyl)-4-(1,1-difluoroethyl)pyrimidin-2-amine (2.0 g, 6.1 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (1.79 g, 6.09 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (0.249 g, 0.305 mmol) were combined in a flask. 1,4-Dioxane (30 mL) and aqueous sodium carbonate (9.1 mL, 18.3 mmol, 2.0 M in water) were added, and the resultant suspension was heated to 100° C. for 4 h. The mixture was allowed to cool to room temperature and then filtered, and concentrated under reduced pressure. Purification by gel column chromatography on silica (10-100% ethyl acetate/hexanes) afforded 4-(1,1-difluoroethyl)-N-(3-methyl-5-(1H-pyrazol-4-yl)phenyl)pyrimidin-2-amine as a brown solid. MS ESI calc'd. for C16H16F2N5 [M+H]+ 316. found 316. 1H NMR (500 MHz, DMSO-d6) δ 12.91 (s, 1H), 9.83 (s, 1H), 8.67 (d, J=4.9 Hz, 1H), 8.04 (s, 1H), 7.84 (d, J=18.9 Hz, 1H), 7.78 (s, 1H), 7.32 (s, 1H), 7.08-7.02 (m, 2H), 2.28 (s, 3H), 1.98 (t, J=18.7 Hz, 3H).

Provenance & Evidence