2-Amino-4,6-dichloropyrimidine → HCID 51354897, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL sealable tube under argon were combined (4-cyano-3-fluorophenyl)boronic acid (0.50 g, 3.03 mmol), 4,6-dichloro-2-pyrimidinamine (0.497 g, 3.03 mmol), saturated aqueous NaHCO3 (4.04 mL), and 1,4-dioxane (16.2 mL), and the mixture was degassed with argon for 5 minutes. Pd(Ph3P)4 (0.175 g, 0.152 mmol) was added, the vial was sealed, and the reaction mixture was stirred for 16 hours at 95° C. The reaction was cooled to room temperature, filtered through a plug of celite503, and concentrated. The resulting orange tar was partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. The resulting orange solid was sonicated in CHCl3 (50 mL) for 2 minutes. The mixture was filtrated, the solid was washed with CHCl3, and the filtrate was concentrated. Flash chromatography on SiO2 (40 g) of the resulting residue (gradient: 100% CHCl3 to 5% EtOAc/CHCl3) afforded the title compound (267 mg, 32%) as a yellow solid. LC-MS (ES) m/z=249 [M+H]+.

Provenance & Evidence