Isoamyl Nitrite → HCID 67252235, compound

Participants

Reaction Steps

To a solution of (R)-2-(2-amino-4-(4-fluorophenyl)thiazol-5-yl)-7-ethyl-8-isopropyl-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 318, 0.25 g, 0.586 mmol) and copper cyanide (0.054 g, 0.598 mmol) in 19 mL of anhydrous acetonitrile, isoamyl nitrite (0.1 ml, 0.751 mmol) was added. The reaction was placed in an oil bath set at 90° C. under condenser with N2 (g) inlet. The reaction mixture was stirred for 1 h, then cooled and quenched with water and extracted with EtOAc. The organic phase was collected, dried with sodium sulfate, filtered and concentrated. The resulting material was purified by preparative HPLC to give the title compound. LCMS: 437.1 m/z (M+H)+; ret. Time: 7.85 min (Analytical Method A). 1H NMR (CDCl3) δ: 7.83 (s, 1H), 7.69 (d, J=6 Hz, 1H), 7.67 (d, J=6 Hz, 1H), 7.15 (d, J=8 Hz, 1H), 7.13 (d, J=8 Hz, 1H), 4.33-4.28 (m, 1H), 4.20-4.14 (m, 1H), 3.37 (s, 3H), 2.07-2.02 (m, 1H), 1.94-1.85 (m, 1H), 1.24 (d, J=7 Hz, 3H), 1.13 (d, J=7 Hz, 3H), 0.84 (t, 3H).

Provenance & Evidence