Trifluoroacetic acid → HCID 86663609, compound

Participants

Reaction Steps

To a stirred homogeneous solution of compound 167 (12.3 g, 32.3 mmol) in dry DCM (325 mL) was added trifluoroacetic acid (24.5 mL, 323 mmol), followed by anisole (7.11 mL, 64.6 mmol). The resultant mixture was stirred at room temperature for 70 h and then poured into petroleum ether (1 L) and stirred at room temperature for ca. 30 min. The petroleum ether layer was decanted and discarded. This process was repeated with more petroleum ether (800 mL). The residue left behind was dissolved in acetone/water (1:1, 200 mL) and stirred with 5M NH3 (500 mL) at room temperature for 1 h. The solid was collected by filtration and washed successively with acetone/water (1:4, 5×100 mL) and then petroleum ether/ethyl acetate (3:1, 5×100 mL) before being dried in vacuo to give N4-(3-ethynylphenyl)pyrido[3,4-d]pyrimidine-4,6-diamine (169) (8.56 g, 98%), mp 220-225° C. (decomp); 1H NMR δ [(CD3)2SO] 9.69 (s, 1H), 8.70 (s, 1H), 8.38 (s, 1H), 8.08 (t, J=1.7 Hz, 1H), 7.95-7.89 (m, 1H), 7.40 (t, J=7.9 Hz, 1H), 7.34 (br d, J=7.7 Hz, 1H), 7.16 (s, 1H), 6.25 (s, 2H), 4.17 (s, 1H). Anal. Calcd for C15H11N5.2H2O.0.2CH3COCH3: C, 60.65; H, 5.29; N, 22.67%. Found C, 60.54; H, 5.01; N, 22.56%.

Provenance & Evidence