Sodium Bicarbonate → HCID 51353297, compound

Participants

Reaction Conditions

Reaction Steps

In a microwave reaction vial, 2-chloro-5-(tetrahydro-2H-pyran-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (0.0258 g, 0.079 mmol), 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (0.024 g, 0.087 mmol), PdCl2(dppf) (0.012 g, 0.016 mmol) and sodium bicarbonate (saturated solution) (0.3 ml, 0.079 mmol) were suspended in dioxane (0.794 ml). The suspension was heated by microwave irradiation at 100° C. for 1 h. The reaction mixture was cooled and purified by preparative HPLC (eluting with 15-25% ACN (containing 0.035% TFA) in water (containing 0.05% TFA) using a Sunfire Prep 5 μm C18, 75×30 mm column). The clean fractions were combined, concentrated in vacuo and lyophilized, affording the title compound (10.0 mg, 28.7% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56-1.73 (m, 2H) 2.61-2.70 (m, 3H) 3.01 (td, J=12.82, 3.66 Hz, 1 H) 3.35-3.46 (m, 1H) 3.46-3.62 (m, 3H) 3.74-3.89 (m, 1H) 3.89-4.04 (m, 2H) 4.14-4.30 (m, 4H) 4.38 (ddt, J=11.81, 7.89, 4.04, 4.04 Hz, 1H) 4.48 (d, J=12.13 Hz, 1H) 6.13 (br. s., 1H) 7.52 (d, J=8.84 Hz, 2H) 8.13-8.20 (m, 2H) 8.40 (s, 1H) 8.81 (s, 1H). MS [M+H] found 439.4.

Provenance & Evidence