Sodium Bicarbonate → HCID 51353297, compound

Participants

Reaction Conditions

Reaction Steps

In a microwave reaction vial, 2-chloro-6a-methyl-5-(tetrahydro-2H-pyran-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (0.046 g, 0.136 mmol), 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (0.041 g, 0.149 mmol), PdCl2(dppf) (0.020 g, 0.027 mmol) and sodium bicarbonate (saturated solution) (0.3 ml, 0.136 mmol) were suspended in dioxane (1.36 ml). The suspension was heated by microwave irradiation at 100° C. for 1 hour, then heated by microwave irradiation at 120° C. for an additional 30 minutes. The reaction was purified by preparative HPLC (eluting with 20-30% ACN (containing 0.035% TFA) in water (containing 0.05% TFA) using a Sunfire Prep 5 μm C18, 75×30 mm column). Product containing fractions were combined, concentrated in vacuo and lyophilized, affording the title compound (41.4 mg, 67.4% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.32 (s, 3H) 1.55-1.74 (m, 2H) 2.62-2.70 (m, 3H) 3.25 (td, J=13.14, 4.04 Hz, 1 H) 3.34-3.45 (m, 1H) 3.47-3.72 (m, 3H) 3.87-4.00 (m, 3H) 4.06 (dd, J=11.62, 3.79 Hz, 2 H) 4.19 (dd, J=13.77, 2.15 Hz, 3H) 6.01-6.24 (m, 1H) 7.48-7.57 (m, 2H) 8.13-8.22 (m, 2 H) 8.48 (s, 1H) 8.81 (s, 1H). MS [M+H] found 453.4.

Provenance & Evidence