Cesium carbonate → N-(2,6-dichloropyridin-4-yl)pyrimidin-5-amine

Participants

Reaction Conditions

Reaction Steps

4-Amino-2,6-dichloropyridine (1.23 g, 7.55 mmol, 1.20 eq), 5-bromopyrimidine (1.0 g, 6.3 mmol, 1.0 eq), Cs2CO3 (2.87 g, 8.81 mmol, 1.40 eq), Pd2(dba)3 (289 mg, 0.503 mmol, 0.0800 eq), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (437 mg, 0.755 mmol, 0.120 eq) and dioxane (16 mL) were added to a microwave vial. The vial was purged with argon, capped and heated at 100° C. for 18 h. After cooling the reaction was filtered over a plug of celite and the plug was washed with 5% MeOH/CH2Cl2. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 938 mg (62%) of the title compound as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 9.57 (s, 1H), 8.95 (s, 1H), 8.76 (s, 2H), 6.95 (s, 2H); [M+1]+: 241.1.

Provenance & Evidence