Potassium Phosphate, Tribasic → 4-[(benzyloxy)methyl]-5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(difluoromethyl)-N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrimidin-2-amine (111 mg, 0.307 mmol), 4-[(benzyloxy)methyl]-5-[(4-bromo-1H-pyrazol-1-yl)methyl]-1,3-oxazolidin-2-one (109 mg, 0.298 mmol), potassium phosphate tribasic (239 mg, 1.13 mmol), and Pd(dbpf)Cl2 (4 mg, 0.006 mmol) in dioxane (2 mL) was stirred and heated to 110° C. in a microwave reactor for 30 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by prep-TLC (ethyl acetate/petroleum ether) to give 4-[(benzyloxy)methyl]-5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-1,3-oxazolidin-2-one. MS ESI calc'd. for C27H27F2N6O3 [M+H]+ 521. found 521. 1H NMR (400 MHz, CD3OD) δ 8.60 (d, J=4.8 Hz, 1H), 7.99 (s, 1H), 7.84 (s, 1H), 7.77 (s, 1H), 7.40 (s, 1H), 7.38-7.26 (m, 5H), 7.15 (s, 1H), 7.05 (d, J=4.8 Hz, 1H), 6.56 (t, J=54.4 Hz, 1H), 4.88-4.76 (m, 1H), 4.54 (s, 2H), 4.48-4.46 (m, 2H), 3.94-3.92 (m, 1H), 3.48-3.46 (m, 2H), 2.35 (s, 3H).

Provenance & Evidence