Toluene → HCID 24901900, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3,4-dioxolanephenylboronic acid (0.938 g, 5.54 mmol) and 2,4-dichloropyrimidine (1 g, 6.65 mmol) in toluene (112 mL) were added 1,4-dioxane (14 mL) and PdCl2(dppf).CH2Cl2 (0.452 g, 0.554 mmol). The mixture was purged with argon for 15 min after which a 2M aqueous solution of Na2SO4 (28 mL, 56 mmol) was added. The reaction mixture was stirred at 75° C. for 24 h, cooled to rt, and then washed with saturated solution of NaHCO3. The organic layer was separated from the mixture, and the aqueous phase extracted with EtOAc. The combined organic phases were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was then purified by silica gel flash chromatography (1:5 EtOAc/Hexanes) to give the product (324 mg, 25%) as crystalline white needles. 1H NMR (400 MHz, acetone-d6): δ 6.15 (s, 2H), 7.18 (d, 1H), 7.70 (d, 1H), 7.84 (d, 1H), 7.96 (d, 1H), 8.71 (d, 1H); LC-MS: RT=2.65 min, (M+H)+ 235.2.

Provenance & Evidence