p-Toluenesulfonic acid → HCID 68181830, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-N-(2-amino-5-bromo-4-fluorophenyl)pyrimidine-2,4-diamine (500 mg, 1.68 mmol) in methanol (6 mL) and THF (20 mL) was added trimethyl orthoformate (5.59 ml, 50.32 mmol) and TsOH (0.03 ml, 0.17 mmol). The reaction mixture was stirred at 70° C. for 1.5 hr. Reaction had only progressed 6% by LC-MS. Extra trimethyl orthoformate (6 mL, 54.23 mmol) was added and stirred at 70° C. for 1 hr. Reaction mixture was cooled and sat NaHCO3 (10 mL) was added. The product was extracted with DCM (3×10 mL) and the organics were washed with brine and then dried (Na2SO4), filtered and concentrated in vacuo to obtain title compound as a beige solid (500 mg, 63.8% yield); 1H NMR (500 MHz, DMSO) delta 9.17 (s, 1H), 8.97 (d, J=6.7 Hz, 1H), 8.37 (d, J=5.5 Hz, 1H), 7.81 (d, J=9.1 Hz, 1H), 7.20 (s, 2H), 7.14 (d, J=5.6 Hz, 1H); LC-MS: m/z=+309.75 (M+H)+.

Provenance & Evidence