Sodium Bicarbonate → HCID 68194927, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave reaction vial were added 2-chloro-5-(tetrahydro-2H-pyran-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x55, 0.040 g, 0.123 mmol), 1-cyclopropyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (0.041 g, 0.135 mmol), and PdCl2(dppf) (0.018 g, 0.025 mmol) in saturated aq sodium bicarbonate (0.3 mL, 0.123 mmol) and dioxane (1.232 mL). The resulting suspension was heated by microwave irradiation at 100° C. for 1 hour, then filtered, and purified by preparatory HPLC using a 20-30% CH3CN gradient in H2O (with 0.05% TFA). The fractions were combined, concentrated in vacuo, and lyophilized to give the title compound as a white solid (13 mg, 23%). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.45-0.62 (m, 2 H), 0.71-0.86 (m, 2 H), 1.66-1.82 (m, 2 H), 2.55-2.84 (m, 3 H), 3.17-3.40 (m, 2 H), 3.46-3.78 (m, 4 H), 4.07 (td, J=12.19, 4.17 Hz, 3 H), 4.30-4.46 (m, 2 H), 4.55 (dd, J=10.61, 3.79 Hz, 1 H), 4.96 (dd, J=13.64, 1.77 Hz, 2 H), 7.67 (d, J=8.84 Hz, 2 H), 8.01-8.26 (m, 3 H); ESI-MS m/z [M+H]+ calc'd for C24H28N6O4, 465.2; found 465.4.

Provenance & Evidence