1,4-Dioxane → HCID 51352111, compound

Participants

Reaction Steps

A microwave vial equipped with a magnetic stirrer was added 2-chloro-5-cyclopropyl-6a-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (100 mg, 0.339 mmol), 1,4-dioxane (2 ml), 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (141 mg, 0.509 mmol), NaHCO3 (585 μl), followed by PdCl2(dppf) (12.41 mg, 0.017 mmol). The reaction was irradiated in the microwave at 100° C. for 40 min. Upon completion the reaction solution was poured into water and the precipitate filtered. The collected solid was successively washed with water and small amount of ethanol and dried in-vacuo to obtain a solid. This solid was further purified by silica gel chromatography (2 to 5% gradient of MeOH in chloroform). The fractions were collected and concentrated in-vacuo to afford the title compound (27 mg, 0.066 mmol, 19.48% yield) as a white solid. 1H NMR (400 MHz, DMSO-d4, D2O) δ ppm 0.55 (m, 1 H) 0.78-0.92 (m, 1 H) 1.01-1.11 (m, 1 H) 1.12-1.24 (m, 2 H) 1.45 (s, 3 H) 2.65 (s, 3 H) 2.78 (s, 1 H) 3.26-3.40 (m, 1 H) 3.55 (m, 1 H) 3.70 (d, J=11.6 Hz, 1 H) 3.93 (d, J=11.4 Hz, 1H) 4.02 (m, 1 H) 4.30-4.39 (m, 1 H) 7.54 (d, J=8.8 Hz, 2 H) 8.08-8.16 (d, J=8.8 Hz, 2 H) 8.20 (s, 1H). MS [M+H] found 409.

Provenance & Evidence