O-Cresol → HCID 86703929, compound

Participants

Reaction Conditions

Reaction Steps

To an 8 mL screw-cap vial was added tert-butyl N-tert-butoxycarbonyl-N-(6-chloropyrido[3,2-d]pyrimidin-4-yl)carbamate 50-A (0.20 mmol, 76 mg) followed by 2-methylphenol (2 equiv., 0.40 mmol, 43 mg), potassium carbonate (2 equiv., 0.40 mmol, 55 mg) and dimethylacetamide (0.4 mL), and 4-dimethylaminopyridine, 0.05 equiv., 0.01 mmol, 1 mg). The reactions were capped and shaken at 80° C. for 2 h. The reaction was filtered, and concentrated via GeneVac. Crude was then taken up in dichloromethane (0.25 mL), followed by trifluoroacetic acid (0.5 mL). The reaction was capped and shaken for 1 h, then concentrated. Crude was purified by reverse phase HPLC to yield 27 mg of product. 1H NMR (400 MHz, DMSO) δ 8.40-8.33 (s, 1H), 8.17-8.11 (d, J=9.0 Hz, 1H), 7.44-7.35 (dd, J=13.1, 8.3 Hz, 2H), 7.32-7.26 (m, 1H), 7.26-7.17 (m, 2H), 2.17-2.13 (s, 3H). LCMS M/Z (M+H)=253.

Provenance & Evidence