Sodium Bicarbonate → 1-(4-(5-Isopropyl-6a-methyl-6-oxo-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridin-2-yl)phenyl)-3-methylurea

Participants

Reaction Conditions

Reaction Steps

2-Chloro-5-isopropyl-6a-methyl-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (98 mg, 0.330 mmol) was mixed with PdCl2(dppf) (48.3 mg), 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (100 mg, 0.363 mmol) and saturated sodium bicarbonate solution (2 mL, sat.) in 1,4-dioxane (4 mL). The suspension was heated by microwave irradiation at 100° C. for 30 minutes. The suspension was filtered, the solids washed with methanol then DMSO and the filtrate evaporated in vacuo. The resulting solid was purified by mass-triggered preparative HPLC eluted with 20-35% of ACN (containing 0.035% TFA) in water (containing 0.05% TFA) on a Phenomenex Gemini 5 μm C18, 75×30 mm column) to give the title compound (30 mg 22% yield) as a pale yellow solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.55 (m, 6 H) 1.62 (s, 3 H) 2.80 (s, 3 H) 3.50 (td, J=12, 4 Hz, 1 H) 3.68 (td, J=12, 4 Hz, 1 H) 3.79 (d, J=12 Hz, 1 H) 4.14 (m, 1 H) 4.62 (dd, J=12, 4 Hz, 1 H) 4.66 (m, 1H) 7.62 (d, J=8 Hz, 2 H) 8.10 (d, J=8 Hz, 2H) 8.13 (s, 1H). MS [M+H] Found 411.

Provenance & Evidence