Tetraethyl orthocarbonate → 4-(6-Bromo-2-ethoxy-1,3-benzodiazol-1-yl)pyrimidin-2-amine

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Reaction Conditions

Reaction Steps

A mixture of 4-N-(2-amino-5-bromophenyl)pyrimidine-2,4-diamine (652 mg, 1.98 mmol), (triethoxymethoxy)ethane (2.0 mL, 9.89 mmol) and acetic acid (0.09 mL) was heated at 80° C. for 40 minutes. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (5 mL) and washed with saturated aqueous sodium hydrogencarbonate (2×10 mL) and then brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give the crude product as an orange solid 1H NMR (500 MHz, CDCl3) delta 1.55 (3H, t, J=7.09 Hz), 4.71 (2H, q, J=7.25 Hz), 5.21 (2H, br. s.), 7.13 (1H, d, J=5.67 Hz), 7.35-7.42 (2H, m), 8.36-8.40 (2H, m); LC-MS: m/z=+334.00/335.75 (M+H)+.

Provenance & Evidence